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A Beginner's Guide to Gold Digging: Chapter 25
🕑 Added 2025-08-04 17:11:27 +0000 UTCCrispin
Lily’s tongue was in my mouth before I could even open the door to our room. I wasn’t complaining too much, though she did have a habit of not letting me open doors for her that I found very amusing. I shoved the door to the hotel room open, a simple one-bed affair, and my hand struggled to find the light-switch in the cool darkness.
“Leave them off,” Lily purred. “I wanna do it in the dark.”
Fuck, that was hot: she wanted it secret and hidden, concealed from the light of day and any prying eyes. “Naughty girl,” I said.
She hooked her legs around mine, and I lifted her by the ass and threw her onto the bed. Lily wanted it rough. I could do rough. We really ought to talk about something like this before going whole-hog, but sometimes… Sometimes you had to go with the flow.
And I did so love making her scream with pleasure.
“Are we doing this?” I asked. “You healed up downstairs?”
“I think so?” she said. “I want to risk it. I really do. I want you to make me like it.”
I blushed. Then I grinned. Then a brief flash of shame hit me, but I pushed it aside. I could do this. I was ready for this. I’d dreamt of it. Lily wanted it, needed it, yearned for it. She wanted it rough and raw, and deep down that appealed to me as well. I’d wanted her for months, wanted this for years without being able to put a proper name on it…
No, no that wasn’t quite true. There’d always been a name for it. An event in my past that planted the seed of this desire, this need, to take what I want, make a girl realize how badly she needed me. I wanted her to fight back. To hate how much she wanted me. To put up a fight, and give in.
It was okay. I was allowed to want it like this. I’d done roleplay before. I’d gotten my freak on well and truly. And Lily was onboard. Based on the way she panting and moaning beneath my grip, she was downright enthusiastic.
Besides, this wasn’t really a scene, This was just sex. And by all accounts, I was very good at that.
“Let’s break in the new equipment, then,” I said, tugging on the edges of Lily’s dress and lowering it. She wasn’t wearing a bra underneath it, and her magnificent tits were on full display. Nipples erect and perky, globes rippling as I began to suck at them, her moans growing louder and more desperate as I went.
Then, she bit me. Teeth sinking into my shoulder, biting down hard, my skin broke and blood gathered by my collar-bone. I looked at her wicked smile, blood and lipstick mixing together on her mouth, and something snapped inside me. I was always hungry for her, but right then I was STARVING.
“This is the part where you say ‘never do that again,’” she murmured, eyes dark and voice dripping with lust.
“Maybe I want you to do that again,” I said, finishing pulling down her dress and putting it carefully on the other side of the bed. “It gives me an excuse to do this.”
I reached for her panties and shoved my hand inside, thumbing the seam of her sex and reveling in the gushing wetness.
Her back arched, her lips quivered, her eyes rolled back into her head. God, I loved seeing her like this. I’d done this to her. I made her feel things she’d never felt.
She looked at me expectantly. “Well? Are you gonna do that again?”
“I haven’t been properly motivated yet,” I said.
Her response was to fist my shirt with both hands and tear it off of me. The buttons flew everywhere, and she took off the fabric and tossed it to the floor. She scratched at my chest, her newly-long, manicured nails with their pink paint-job raking across my skin and through my body hair. Pain mixed with pleasure, dumping fuel on the fire inside me.
I spread her legs and pulled down her panties with my teeth, kissing her inner thighs on both sides, caressing the mermaid tattoo on her left leg while she kept on clawing at my back. She’d shaved the sparse hair I had there this morning, leaving no obstructions in place. Just sensitive flesh being carved up by pastel pink talons.
I nipped the thigh-flesh to my left and right, then stared her new pussy in the face.
“Would you look at that,” I said. “That is the most beautiful thing I’ve ever seen.”
“I find that hard to believe,” Lily giggled.
“You’re gonna have to take my word on it.”
“Surely you’ve seen prettier pussies.”
“Maybe. But I’ve never seen one attached to you. Far as I’m concerned, that makes it a cut above the rest. I bet you’re just begging for me to eat it, aren’t you?”
“N-no,” she said, not at all convincing.
“Well too fucking bad,” I said before planting a kiss on her sopping-wet front entrance. She tasted like nectar. Like ambrosia. Like honey-whiskey and communion wine. Like something beyond words, because how could mere words describe the most perfect taste in the universe?
She shuddered, her noises growing both softer and more intense at the same time. I licked her, and her back arched again and her toes curled and her claws dug into my back. Just more motivation, as far as I was concerned. I licked and kissed, a favorite activity of mine, long-neglected while I waited for Lily to ready herself for me.
“So pretty,” I said into her sex, “So delicate.”
“No I’m not,” she groaned.
“You are with me,” I said. “You are for me. Maybe that’s why we met. I was the only one who could show you your true self.”
My tongue found her clit while my mouth worked her lips, and she flooded with orgasm on the spot. She screamed, and I heard the one sound I like better than her laugh.
“Well that was fast,” I laughed, rising from her valley and sitting up. “Guess my work here is done-”
“Oh no you don’t!” she said, grabbing me by the waistline of my pants and pulling me back on top of her. She pulled down my zipper. “You’re not going anywhere!” She shimmied my pants off of my legs. “You’re gonna fuck my brains out right fucking now!”
“So needy,” I grinned. “You get one taste and suddenly you’re an addict.”
“Shut up!” she pouted. Her claws were coming back out; I’d have to work extra hard to keep myself safe, which was just how I liked it. The blood on my shoulder and back was coagulating and clotting, but I was ready for some fresh wounds.
“Make me,” I said.
She grabbed a fistful of my hair and tugged on it, and I grunted with sweet relief. My dick was at half-mast, and as Lily pulled off my boxers and started fiddling with my balls, it came to full-attention. She stroked the underside of my shaft, coaxing me towards her slit. She was still soaking wet and quivering, and her soft hands were warm around my sensitive skin.
“God, you’re so big,” Lily said.
“What’s the matter? Never seen one that big before?” I played along.
“No. I don’t know if I can take it all,” she pouted.
“Guess we’ll just have to find out,” I said. “But I think you’re more than up to the task.”
“How do you know?”
“You’re my angel,” I said, kissing her cheek, her temple, her neck. “I know you’d do anything to please me. Even if it means taking me all at once.”
Genuine panic flashed across her face, and I nearly fell out of the lusty headspace. “Hey,” I said, “What’s wrong? What’s going through your head?”
“Just… Just nervous,” she said. “What if I don’t like it? Then all this was for nothing and I’m just… I’m just nothing.”
“You’re everything, Lily,” I said. “Just tell me how you want it, and I’ll give it to you. And hey, you’ll never know until you try.”
Her smile, the only light in the room, the only light I needed to see by, came back. “Okay. Let’s just… Let’s just start slow, okay?”
“You set the pace, angel,” I said, kissing her mouth. “I’ll do my best to keep up.”
She nodded, then gripped my length once again and guided it towards her slit. She stroked my head, rubbing it against her vaginal lips and trembling with delight as the sensations gently coaxed her out of her shell. My foreskin tingled with ecstasy as she slowly guided me inside her, a tiny bit at first, before gradually letting the entire head in. She purred, letting go of my shaft and returning her long nails to the holding-points she pressed into my back, and I started moving my hips forward. A little more, then a little more, then a little more. She was tight around me, slick and wet everywhere, and the sensation was pleasure I’d known before but never quite like this. Taking it bare, slowly taking more and more of it, she hummed and sang and shifted about as I pushed myself inside her.
It was like a button labeled ‘warm pleasure’ was being held down inside my mind. Someone had put a paperweight on top of it, and now all I could feel was bliss.
I was halfway inside her, and threads of ecstasy were running up from my dick to my brain. She kept on clawing at me and biting me, over and over again, and it lowered me deeper and deeper down into the mindset I’d long neglected.
My partners rarely asked what I wanted. Rarely bothered to find out. Never stuck around long enough to utilize the information once they had it. I liked the sex, always had, but after a certain point it had become work for me, and a dream job is still a job. But with Lily, oh Lily, my naughty, subby little fiance, there was nothing work-like about it. This was living the dream.
“More,” she begged.
“Oh?” I said. “Ask me like a good girl.”
“More, please! Master!”
I’d bet good money my pupils dilated in that moment as a fresh wave of strength and lust crashed into me. God, I really had her totally under my spell. Wasn’t that… Wasn’t that wrong though? No, no it was fine. We were consenting adults, she was into it, the whole thing had been her idea… And besides, I’d done stuff like this before. Never with a girl like Lily, admittedly, never with a girl who I’d been this serious about… But I’d done this before and enjoyed it. So I ought to let myself enjoy it!
She nipped my earlobe, and my levees of resistance crumbled beneath her seductive tide. A pelvic-thrust later, I was eight-inches deep inside her, the threads of pleasure now a river running straight through me. I lost myself in her, tongue her mouth and rod in her pussy and hands on her tits. She moaned and screamed into me, thrusting her own hips forward and pressing her legs together to take as much of me as she could. Like she wanted me inside her always, filling her, completing her. She fit around me perfectly, and I fit inside her perfectly. Like we were made for each other.
“So tight,” I said into her mouth, my bucking growing harder and faster. I was a starving man, and she was a feast. “So good. So perfect. So… So delicate. I’m the only one who can handle you properly, aren’t I? The only one who knows how to get past your defenses, how much force to apply, how much care to take. The only one who knows how soft you really are underneath all those hard edges.”
“Yes, master,” she purred, legs around my back, nails tracing the outline of my tattoo. “You’re the only one for me.”
“Good girl,” I said, going faster, faster, pinning her hands behind her head.
I started welling up with orgasm, getting closer and closer with each stroke, but I held it back. There was no way in hell I was finishing first. If we could finish at the same time, though, that would be amazing. So I rotated, bent my hips so I was running directly against her clit, hammered her g-spot over and over again.
“Master,” she said, and I felt her tighten around me evermore. “Oh, Master. Please… Please… PLEASE-”
“Please what, angel?”
Her lips touched my ear, and she whispered three little words to me. Three words she knew not to say, but was too drunk on me to keep bottled up. Three words I’d dreaded hearing. Three words that lanced my chest and carved up my insides. Three words that disemboweled my soul, tore me out of the lusty, dominant headspace and sent me plummeting to the bottom of a deep dark abyss. The world around me became hollow and black, all the noise turning to static and all the scents and sensations fading away.
Lily finished tightening around me and came again, but I barely noticed. I slid out of her and rolled off of her, unable to hear what she was saying to me. I vaguely registered the look of concern sprouting on her face, but as I rolled onto my back and stared up at the dark ceiling, that fell away too.
All I felt was that guilt and shame, acrid and jagged and visceral, pulling me down deeper and deeper and deeper into the dissociative pit of unreality.
She held me tight, seemingly not sure what else to do, while I laid flat and looked at nothing, horrified by the fact that I’d well and truly become That Guy. Horrified by the fact that for a minute there, I’d liked it. Horrified by the fact that I’d betrayed everything I’d promised Naomi, promised Julia, promised myself, promised God I would be for the sake of my own pleasure.
I was scum. I was a sinner. And I’d done it to myself, every step of the way.
And I’d done it to Lily, too.
She stopped trying to talk me out of it after a few minutes, which was good because I couldn’t discern what she was saying. I felt her holding me, but I didn’t deserve her.
I never had. And I never would.
