What Happens in the Dark Ch. 01

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A jaded man takes what he wants from an unlucky chosen bitch.
8.6k words
4.5
42k
67

Part 1 of the 4 part series

Updated 03/04/2024
Created 06/14/2023
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Chapter 1

You know, people think having money would make your life SO simple. Yeah, it makes some things easier, but some things it makes hella complicated.

I stared at all the bitches jogging in the park. They were mostly broke nothing whores with no life plan, no real ambitions, and wanting nothing more than men to give them everything because they had an ass and tits. They pissed me off.

It had been three years ago. I'd been a young business major in college. My friends and I were getting back from a road trip during spring break and had, as a joke, bought powerball lottery tickets. Paid the 'poor tax'. Nobody really ever won those. It had been two weeks before the drawing had happened. Then the craziest thing happened.

I won. Steven Lewis, the nobody, had won.

20 years old and I now had $650 million dollars. Okay, so a lot less once taxes came out, but still more money than I needed to last the rest of my life if I played it smart. And since it was coming up one of my professors had even done a class on "what to do if you win the lottery".. So I did exactly what he said to do. I got a lawyer, claimed the winnings anonymously, got the taxes taken care of and invested intelligently.

My friends hadn't bothered to learn my lottery numbers, so they didn't know. I didn't tell my family. No one had a clue. I pretended to go to college, and the fact that my graduating class didn't get a graduation ceremony because of the fucking pandemic.

I bought a reasonable house, (fuck the housing prices) just big enough for a wife an a few kids. I figured any woman would be all over me for my money, but I didn't want a freaking gold-digger. So I pretended to be an accountant, keeping who I work for as discreet as possible.

Turns out, being stingy with details about your employment made all the hotty bitches assume you were a dead beat. Didn't matter that I had a gym membership and all the time to work out and was in peak health. Didn't matter that I had a nice care. Didn't even matter that I had a nice seven inch dick with a nice girth that none of the girls I had been with had anything but good things to say about. I even loved eating pussy and making my girl cum so hard she screamed.

Nope, these fucking bitches didn't care. Three years and I hadn't had a date in two of them and the last date I'd had all I had been to her was a meal ticket. She'd even brought a fucking friend to eat on my dime.

I'd been fucked over one to many times. And while I considered myself a reasonable man, I started to understand where the crazies came from. I started making plans. I found out exactly how much remodeling I could do without a permit and put my plan into effect. I broke my remodeling of my basement into four sections, using a different handyman each time. I claimed I was making a man cave. I even filed it with computers, TVs, game stations and fully decked it out. I did give each of the contractors a Nondisclosure agreement and they had agreed to keep my man-cave secret. I'd claimed I had great reviews for each of them, and paid through the nose to get out of town contractors and people that would be basically impossible to find.

Finally it was done. Then I started rearranging things and preparing and the golden sign from on high came. The last handyman got hit by a drunk driver. His wife would be taken care of by his life insurance and the sizable payment I gave him would hold her over. One of them moved to Europe. One suffered a cardiac incident and passed away. The final one was retiring and announced he had been diagnosed with early onset dementia, nothing he said would be taken seriously.

Now my man-cave could transform to its true purpose: a sex dungeon.

Yep. I found myself deciding that until I found a woman willing to give me a chance, I'd take the fucking choice away from the fucking bitches. I even had a particular bitch in my sights.

Her name was Karen. Karen Johnson. And damn did she live up to the Karen stereotype. She was a certified grade-A bitch. Snapped at everyone. Rude, demanding, and loved exploiting poor guys who wanted a chance because the one thing she had was looks. She had flawless breasts, a perfect ass, amazing skin, full luscious lips designed to wrap around a cock. And she was one of the fucking feminists that didn't care about actual equality, nope, to her feminism was just a tool to oppress men and get what she wanted. She was twenty-two, just graduating from college and had coasted on the privilege of her gender all her life.

It had taken me months to line everything up. I had learned her schedule, which had been far too easy, and when she was graduating and when her new job started. It was perfect. She was planning a two month long road-trip after graduation until her new apartment opened up. That was when I'd do it. She'd be mine and no one would question her absence since she was going to be "on a road trip". I'd have two months to have my way with her.

Now, I wasn't a killer. I'd release her when I was done, but fuck, she was to me the epitome of everything wrong with women today and I was going to break her.

That's why I was here today. I had everything set up. I'd even sabotaged her dinner reservation to make sure she came for her evening run later than normal. She'd wanted to have a last dinner at her favorite restaurant before she left, but she religiously ran each night. I'd even managed to sabotage another of her evenings to make sure she'd still do her run through the park.

There she was. Pulling in as the last car pulled out. From my position on this unlit bench I could see her walk into the park under the light at the entrance. She put in her earbuds, tightened her shoes and started to jog.

I got in position. It was a mile long loop around the outskirts of the park. I hid in the trees near the end of the path, where the only thing in earshot would be closed businesses and empty parking lots. I waited to hear her jogging footsteps in the dark. Then just when she passed I made my move.

I leapt out and grabbed her around the waist with one hand and put the damp rag in my other hand over her mouth to muffle the scream. She tried to kick me off but I got a hold of both of her wrists and had her arms ensnared. Her legs flailed as she tried to kick her way free. She kept screaming into the rag not realizing that the smell she was inhaling as she screamed was chloroform.

I'd done my research. I knew it would take minutes for a person to succumb. That was precisely why I'd chosen to do this the way I had. She was exhausted from her run, and blind in the dark between streetlights. She was breathing hard from her run and harder to try to scream. A minute felt like a long time, but her struggles got weaker and weaker, then she finally flopped.

I immediately took the rag from her face. Based on the amount of screaming she'd done, she'd be out. I had no fear of that. All I had to be careful of now was getting everything done before she woke up. I put her arms behind her back and put padded sex handcuffs, the rare ones without an easy release on her hands and linked ankle cuffs on her legs. I estimated I had five minutes to spare in the window I had prepared.

I pulled her phone from her arm strap and used her thumb to unlock it.

I checked her texts to see if anyone was waiting for her. There was a text from someone named Katie, "It's late, where are you?" Followed by Karen's response. "I got held up at dinner, going for my run then I'll be home." Followed by Katie's response of, "Fine, I'm going to bed. And I'm not getting up in the morning. So enjoy your trip."

Her roommate. I'd never had a name. It was good to know she was going to bed and didn't expect to be awake for Karen returning home or leaving in the morning. I realized a roommate was the one thing I'd overlooked, but fucking luck had my back.

I looked for social media and posted on each of them that she was so excited to go on her road trip starting tomorrow and how she was going to unplug from social media during it to truly "refresh myself and prepare to enter the big world as a college graduate!" That ought to keep people from expecting updates and selfies.

I quickly removed her passcode to unlock her phone, using her finger again to verify. I wanted access later, when I could safely peruse her phone at will, but for now that was all I needed. I powered her phone off, then tucked it into the faraday bag I'd gotten to make sure it didn't give my location up. It would block all signals to or from her cell phone until I was ready to take it out.

I carried her back to her car, avoiding the lights the whole way, but cutting across the lawn was easy enough. I grabbed her keys from the strap she had them on and took over her car. I had planned on putting her in her trunk, but I realized to my pleasure that her bags were already packed and in the trunk for her trip the next day. This would mean that her roommate wouldn't have any suspicions, but it did increase the risk of being seen with an unconscious and cuffed woman in the back seat.

I flopped her in the back seat and hopped in. I wanted to get where I couldn't be seen as fast as possible. I took lesser used and lesser traveled roads, and didn't relax until I was pulling into my garage at home. Once the door was closed no one could find her car here without a search warrant and I'd been careful to make sure I left no traces to give me away. Plus, since she was going to be "on a roadtrip" no one should even come looking for her before I set her loose. The drive had been ten minutes, and I had roughly another five to ten minutes to get her setup how I wanted her before she woke up.

I took a second to finally feel those fabulous tits. Oh god, they were better than I'd hoped, firm, supple and begging for attention.

I hoisted her on my shoulder and carried her down to my sex dungeon. The entrance was behind a false bookshelf, with a mantrap system set up so you had to go through one door, let it close, then you could open the other door. Once inside, I quickly removed her cuffs, then carefully removed her clothes. I'd need to put her back in them when it was time to release her. Then I took her to my prepared setup. I'd paid a visit to the BDSM section of a few of the local sex shops and I took little time to strap her into the restraint frame. Her ankles, knees, hips, neck, elbows and wrists were strapped in. She was now restrained, kneeling on pads with her arms held safely at her side, her legs spread wide. I slipped a silicone ring gag that would keep her mouth open and let me enjoy the pleasures of her mouth and would prevent her from biting me or keeping her mouth closed. A blindfold completed the set.

I sat back to admire my handiwork. The now naked beauty was ripe for the taking. I took her clothes and put them inside the mantrap. The hinges were not exposed and the sturdy handle would give her no way to break free. I'd had to swap out the straps on the frame, otherwise she could get loose and while I didn't intend to keep her strapped in that position for two months, I was going to give her several solid fuckings before I let her out.

I moved behind her and with a smile reached down to start stroking her pussy. My personal cum dump for the next two months. The soft velvety lips sent lightning up my fingers. The feeling of dominance was amazing. This woman, this fucking bitch, was mine. I'd use her however I wanted. I felt around to explore my new treasure.

Karen was still unconscious, but her body began to respond to my touch. Moisture began preparing her cunt for the railing it was about to receive.i found her clitoris and rubbed it, smiling as she made pleased noises, despite the gag garbling her sounds. I slipped my fingers inside her and stopped in shock. There was no way.

Karen was a fucking virgin.

Unless she managed to find a cock smaller than my two fingers, nothing had been in there. One finger could barely slip through the opening of her hymen, so maybe she's put tampons in there. Holy shit I was giddy. I was changing this reddit fucking now. I'd planned on waiting for her to wake up to fuck her, but damn this changed things.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

(Karen)

It was a nice little dream. I couldn't seem to remember how it started, but there was a pleasant sensation on my vagina, like gentle waves of a nice, pleasant gentleness roaming my surprisingly sensitive womanhood. I'd never had a dream like this before. It was nice. I wished I could have this more often. The pleasantness got better as the sensation entered me, only the slightest bit, I wished it would go further.

Then a foggy place in my head seemed to have a realization. Something wasn't right. There was some sort of strap wrapped around my head and my tongue found a ring of some kind, right behind my teeth, holding my mouth open. Then I noticed I was blindfolded, that was silly. Why would I be blindfolded? I went to reach up and remove it only to notice, I couldn't move my arms. Or my legs... Or anything. I was almost completely immobile, all I could do was wiggle a little bit.

Then the memories began to return. Dinner getting pushed late after I packed my car so I could leave super early in the morning. Deciding that, since I lived in a nice safe area, and there were only a few dark places on my job, I'd do it despite how far back it had been pushed. After all, I was a strong female and I wasn't afraid of anything. Then during my run, the dark figure leaping out and catching me. That stinking rag, the struggle, then nothing.

I began to panic, I'd been kidnapped!

... and now something was touching my pussy! OH GOD!

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

(Steven)

Karen began to stir as I made my discovery. Initially groaning and pushing her pussy back into my fingers. Then I saw her slowly realize what was going on, struggle, then she tried to pull her pussy away from my stimulating fingers, but the rack made that impossible.

If anything, her pussy became wetter.

I dropped my jeans and boxers, my dick needed no more encouragement and I knelt behind my restrained virgin. I slid my cock up and down her slit, getting moisture on it, then not bothering to be gentle I slid my dick into her baby maker. Her lips parted and allowed my rod into her intimate depths. I hit her hymen and held there for a second before grabbing her hips and slamming myself balls deep. The satisfying pop of her hymen getting obliterated drove me feral.

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(Karen)

I felt the tingling in my vagina increase. What was going on? Was this? Was I getting turned on? No, that can't be right.

There was a brief moment of release from the stimulation, then something much thicker began rubbing my folds. Oh, why did it feel like this? It felt so good! I could feel myself waking more and more. My mind latched onto the realization, I was being raped! But my traitorous body insisted it felt good.

Whatever it was forced its way into my delicate opening, stretching it like I'd never felt before. Oh god... Why did that stretch feel so good? Then I felt tightness inside me, like the intrusion had entered as far as it could. The intrusion stopped. Thank god. I was not at all used to any of these sensations, and though my mind knew I was being violated, the tingling of my body, and an almost aching sensation I'd never felt before, were really confusing me.

Then I felt the hands, rougher this time, grabbing each of my hips and my vagina exploded. The tightness released like a rubber band drawn too tight, with a sharp pain, then the intrusion filled me deeper and more fully than I'd ever known possible. It hurt and felt good at the same time. The stretching was making my mind spin, and the lightning of nerves I'd never felt filled me. I tried to cry out, but the ring made it unintelligible as the rod began bucking in and out of me, amplifying the sensations and making all thoughts stop.

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(Steven)

Karen shrieked as her virginity was obliterated, and I started thrusting with abandon. All the years of abuse and ridicule by women who thought they were better then me fueled me as my hands held her hips and my balls slapped her pelvis. Karen began grunting with each thrust, sounding more and more turned on and pleasured as the fucking went on, and I realized the bitch was getting off on this. Just before I hit my peak Karen squirmed against her binding, then fell limp again. The damn cunt had climaxed before me.

I thrust in and emptied my balls into her. The first of many loads of my cream that would fill her snatch. I pulled out and looked down at the glorious mess I'd made of her pussy. Karen shuddered as the moisture filled her newly split baby maker.

Fuck, that was great.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

(Karen)

Every single good feeling possible went off in my brain at once. If I hadn't been bound hand, foot and body, I would have thrashed uncontrollably as my muscles spasmed beyond my control, but instead I just pulled against my bounds. That sensation was amazing! My mind still refused to do anything but try to process all the strange and powerful sensations rippling through me.

After an eternity in a single second, my mind fluttered back awake. I was still blindfolded, mouth forced open and drooling. I was still bound. I was still being raped.

I felt the dick pumping and out of me accelerate. I could feel my captor's hands on my hips, gripping me with urgent need. I realized to my horror what was about to happen, and worse, I could hardly wait to see what it felt like!

My guess proved correct and the long hard rod jammed deeper in me than I would have thought possible and it spasmed. Warmth blossomed deep in my womb, filling me in a way I could never describe or explain. Then it spread into my vagina, around the cock spurting deep into my core. I realized I was pushing back into my captor, begging for more. The sensation triggered something in me and although my skin felt cold and exposed, every part of my body felt the warmth from deep in my womb.

The rod stayed embedded in my vagina for what felt like an eternity, a soreness slowly creeping in. Then finally it was removed and I felt a sad emptiness I had never experienced before. I never wanted to have sex again, but at the same time, I would give anything to fill that emptiness again. What was wrong with me?

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(Steven)

I savored the feeling of her pulsating depths, then finally pulled out. I should probably clean up the blood. She'd be coated in enough cum, and I only intended to wash her off occasionally, so the cum didn't bother me. The blood though, that could be bad. I retrieved some wipes and cleaned the blood from her deflowered opening.

I popped one of the pills I'd nabbed to help me stay hard. I wanted to have fun with my bitch and this would be the best time with her.

I looked around the room.

I'd padded the walls and floor so she couldn't hurt herself and I could be as rough as I wanted and not worry about it. The only thing that could potentially be dangerous was the toilet. It was as small as I could get and tankless. It was one of those fancy models that you could set limits on. She could only flush once per hour, that way she couldn't just let the water run and rack up my bill. Not that she'd be down here alone very often. I only had my cum dumpster for a month and I planned on using every minute of it.