The Boss - Part 2 "The Trick"

Hey, there.

This is a fictional dark fantasy story that will contain romance and some vanilla parts to it, but mainly consists of blackmail, rape, and violence. I don't condone or partake in any of the actions portrayed here.

This is for people like me, guys and girls, who like this kind of harsh stuff with a good story. For those of you out there, enjoy.

***THIS STORY CONTAINS FICTIONAL RAPE, BLACKMAIL, AND VIOLENCE. READ AT YOUR OWN DISCRETION. YOU’RE WARNED.***

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Part 2 - “The Trick”.

You know, when you are experienced at doing things like this, you don't usually get carried away. You think meticulously, as you try to get the best results possible, even when you are excited, or nervous, or worried about the outcome. It is the same of when you try to close a big business deal. You can't show all your cards, and you shouldn’t go all in if you don't know for sure you have the winning hand. I had three possible options available at the moment.

One possibility was too keep fucking Alissa. That's what I actually wanted to do. Just by having her there in my arms for a minute, caressing her young body while she trembled like a scared little animal, made me hard again in no time. She most certainly could feel my erection rubbing against her bare bottom. I undid her bra, tossing it onto the rug near the rest of her clothes, and I played with her young breasts. Though they weren't big, they were firm, and they fitted my hands perfectly. Her nipples were almost the same tone of her bright skin, but with a light tone of pink, and they were erect, as it should be. She just sobbed softly as I did it, exhausted. I figured that, if I wanted to fuck her again, she wouldn't have the strength to even try to resist.

The second possibility was to send her home right away. But that's another thing I learned in life. The way you let a night end always influences the way the next days will follow, so if I wanted this to go the right way - and by this I mean controlling this girl and abusing her for the foreseeable future - I had to play my cards right. That's another thing I learned from my business career, never taking anything for granted.

So, I went for the third option. I had her father's mistakes to bring her here, but if I wanted to keep her in the long term, that wouldn't suffice. I had to have something on her as well. And I knew exactly what to do.

"I read everything you have in your computer, you know. I know the way you feel, I know about the fact you're depressed and all of that," I said while occasionally kissing her shoulders. She gasped. "Calm down. You can trust me. I'm good with information. Everything I know about you is just between just you and me."

"I know it will sound ironic, even hypocritical, to say that, but you can trust me. This is why I have to tell you that if you try to kill yourself, our deal is off, and you know what it means."

I couldn't seize her reaction, as she had her back towards me, but her breathing changed into a short, scared one, one I hadn't seen so far.

"Shhh… Calm down," I tried to appease whatever she was feeling, "I'm saying this to be frank with you. As I said, I know you. Better than anybody else, by now. What I'm proposing is another deal. One that works for tonight. Be a good girl, get along for the rest of the evening, and I won't fuck you again today or do anything else to you until it's time for you to go home. And you know I could, as I know you can feel how hard you are making me."

Alissa gasped again, but didn't say anything.

"Will we try that or can I start thinking about how I'll fuck you next? I'm pretty sure you are very sore right now, so think well," I said and bent back a little with her in my arms, so she slid down my chest a bit and I could have a look of the side of her face, "Deal?"

She looked at me, her face red from crying and fear all over it. I repeated, "Deal?" And she nodded.

"Beautiful," I said. "I won't touch you again, but you do as I tell you, and you treat me as somebody that is trying to be good to you."

I got up and gave her a hand so she could get up. The poor girl had a hard time standing, what was beautiful to see. I could also see a line of sperm drizzling out of her lovely slit, and it was stained with blood.

"Sit down. You're going to have a drink with me," I said reaching for the crystal bottle over the center table. My cigar still burned in the ashtray.

"I-I don't drink," she replied softly and inoffensively.

"Nonsense. Like all the good things in life, you have to get used to it," I said while pouring us some in a glass, sipping from it and handing it to her. "Go easy, but drink some."

I said, and she hesitantly did it. I expected a grimace, even though the whiskey was very, very smooth. But, to my surprise, she drank it nicely. Just a sip. Then she gave me the glass back while I sat beside her.

Then I tried to make conversation. I asked things about her that she would be ashamed to answer, things like when she first felt attraction to men, what made her decide to lose her virginity, how was it with the kid, how she hid it from her parents, etc, always giving her the whiskey glass back after I took a sip myself, leading her to think that what I wanted was just a kinky talk.

Soon, the beautiful Alissa was talking to me without crying, and even boasting some confidence. I got some interesting insight on the way she thought, which I'll share with you in a future moment, but the good part was that she had fallen in my trap.

I made very reasonable comments about what she said, very comprehensive all the time, and she was noticeably feeling more comfortable, as she trusted that I wouldn't do anything to her that night anymore, which was true… to a certain extent.

After half an hour and noticing her getting groggy, I said "This is really nice. I'm having a really good time with you. See, that wasn't bad at all. Now I just want to ask you to do something…" and soon as I noticed her getting stiff again, I added "Don't worry, no sex and no touching involved."

I got up to the place I was before, where I fucked her, in front of the couch, and now facing her.

"I just want to have another good look at you, and you'll show me that you trust me. A leap of faith of sorts," I said giving her my hand, she hesitantly took it and got up. "Can you do it again? Bend forward and show me your beautiful little pussy?"

Alissa cringed when I said that, and I loved it. She thought about it for some seconds. When she looked about to start crying again I begged her not to, saying that everything was ok, that I had hurt her enough tonight. Apparently, that was enough to comfort her. The beautiful girl turned around and, shaking, bent forward all the way until her head and arms were on the couch. There it was again, that beautiful, tight, heart-shaped ass, and that oh-so-tight young pussy, even though I could see how it was still gaping a little bit due to how hard I pounded it half an hour ago.

"You are so beautiful…" I stated yet again, and she ashamedly hid her face, pressing it against her crossed forearms laying on the couch. It was enough time for me to, silently, get a hold of my phone. I put the camera on behind her back and started talking to her. "You are such a sight, you know? I know you probably don't want to hear this, but I'm really glad I have you here."

She didn't reply, as expected.

Then I said, "I want you to tell me you love doing it with me, in a way I believe it. Use your words. Say you're my whore, and I'll let you go home. I promise."

She inhaled deeply.

"No crying, I added. Make me believe, and you're on your way home."

"I-I love fucking with you. I'm your whore." Alissa said awkwardly.

"That's not enough. Come on! You can do better! I'm being nice to you!" I said with a little laughter.

She sighed, sounding a little more comfortable with the situation. I pressed the record button, as the camera caught her beautiful body and a little of her face, no longer covered by her arms.

"I loved having sex with you, Mr. Cagliari.”

"Oh, you did, pretty thing?"

"Yes. I'm your whore."

I felt excited. Really excited. Her voice sounded adorable. I wished I didn't have to make her trust me, so I could plunge everything I got into her right away, but I had plans. That didn't stop me from pushing her a little more. I could always edit the video.

"Do you want me to make you cum later on?" I asked, and hoped that she was going for it, doing her best so I'd let her go.

"Yes. I never had an orgasm in my life. Please. Just not tonight. The first time got me so sore… I don't think I can."

"That's my girl."

And that was it. I stopped the recording with a big fucking smile on my face.

I put the phone down without her noticing it, then I touched the side of her butt and she shivered. With a little slap, I added "You're perfect. Thanks for playing along. You just made me very happy. The driver will take you back home, and he will drop you one block away from it so nobody sees you getting there. If you need anything, anything at all, text me on that number I gave you." I said and she promptly got up, picked up her clothes and started putting them on, which I enjoyed watching from my seat at the couch, cigar already back to my lips.

When she was about to leave I stopped her. "Hey, come here and kiss me goodbye."

She looked at me almost in panic, stuck in place for some seconds, so I added "Come on. I won't bite you... Yet."

And Alissa crossed the room fast, looking gorgeous in her black tube dress and heels, bending to kiss me on the cheek, crying yet again.

"Ah-ah," I stopped her again. "Here." I took a finger to my lips.

She looked at me with a mix of fear and disgust on her face.

"Just a peck, come on."

And she kissed me lightly, then she turned around to leave, and I called her again. I asked her to stop for just one second while I called my security, and I reached for my phone. She stood right there, looking at her feet, fidgeting.

I called Brandon first, "Hey, we're done here. Get the car ready." Then I swiftly turned the Bluetooth on, connected to the speakers in the living room, scrolled to the part of the video where I supposed was what I would like to hear and…

"...Loved having sex with you, Mr. Cagliari.”

"Oh, you did, pretty thing?"

"Yes. I'm your whore."

It resounded throughout the whole living room.

Alissa looked at me, her eyes wide again, shock all over her pretty face.

“I’m sorry, I couldn’t leave it just to the memory. Don’t worry, you’ve been a good girl. This is between us. It’ll never see the light of d…”

Before I could finish the girl was already running in my direction, heels and all.

“Y-YOU BASTARD! YOU M-MONSTER!”

She wasn’t very fast, with her wobbly legs from all the fucking, and wearing heels, so I had more than enough time to get up. When she reached for the whiskey bottle over the table I already had my hand around her thin wrist. She was screaming like crazy, when I heard Brandon open the door and rush inside.

“Go back, Brandon! I got this!” I said while twisting her arm and making her fall onto the couch with me on top of her. Brandon knew to trust me, so I didn’t even have to look at him, or say it twice. He just left and locked the door again.

Even though she was thrashing like a mad woman, it wasn’t hard to get a hold of both her wrists and pin them on top of her head, then I slapped her face. Not hard, just a warning. Her head yanked left, and there it stayed, her lustrous and long dark hair splayed all over. She was static, in shock.

“I admire your spirit, girl…” I said through clenched teeth, while I struggled to position myself and put her panties aside, out of the way. “But you shouldn’t have done this. Now I can’t help myself.”

She didn’t fight. She didn’t look at me. She kept looking to the side with a lost glare. I spit on my hand and rubbed my fingers at the tip of my cock, completely hard again, to make this fast. I wanted to be inside of her again as fast as possible.

Wasting no time, I pushed it in again. Alissa winced, and then let out a defeated, agonizing cry. She was as tight as before, but it was easier to get in. In no time I was fucking her viciously. Her young, delicate body, just rocked to my movements while she groaned to every thrust.

“Huungh! Huuuh! Agh Huuuuuh!”

I moaned gladly, savoring my girl. In and out, not taking it completely out, not pushing it completely in either, just fast, hard strokes. Her slender, skinny legs just bounced to the movement, and I even had time to admire the thin line of black pubic hair she had crowning the shape of her young pussy. It was a dream, a vicious dream. She had lost, and she knew it. I couldn’t have hoped for a better outcome. I was dying inside from letting her go home without fucking her again. Now I had that amazing pussy gripping my cock again every in and every out.

“W-What a good g-girl you are,” I said under my breath while fucking her non-stop.

Depending on how hard I pounded, or how fast, her beautiful voice switched from a cried moan to a high pitched groan, tears always running down left, falling over the couch. I bent over her, took the hair out of the way to admire the side of her face, and I kissed her neck, her collar bone. Her smell was amazing, sweet and fruity. In no time I felt an orgasm coming, so I quickened the pace, making her squirm, cry, not uttering a single word.

Then I buried all in once again, and I unloaded everything deep inside of her. Alisssa closed her eyes, shaking hard, and her full lipped mouth turned into a silent “O”, while I grunted loudly.

When I stopped and took my dick out of her vandalized pussy she didn’t react either, just stayed there with her legs spread, one arm falling off the couch, breathing deeply. Cum mixed with a little blood oozed out of her. I just sat at the couch, catching my breath and looking at her.

We stayed in silence for a good minute, while I was back to my cigar. Until she whispered, “Can I go h-home?”

“You can. Give me just one second,” I said, and I walked fast to my study and back with some wet tissues. She didn’t move. I caressed her inner thighs with no reaction on her part, and then started wiping her little pussy clean, while she gasped, still crying. Yet, no resistance at all.

Watching her feeling so embarrassed, so abused, it was one of the most exciting things I’d ever gone through. I was loving that. I tended to her like she was a doll, a gorgeous, and super expensive sex toy. After I cleaned her from all the cum and blood, I put her panties back in place, and I carefully closed her legs. Then I bent forward and hugged the broken young girl, making her sit, while the only thing she could do was tremble and cry.

“Do you want to spend the night? It would be better if your parents didn’t see you like this.”

She finally looked at me, confused, traumatized. “I-I c-can’t.”

“Of course you can. You have a room here already, with anything you might need. I even had the walk-in closet set with clothes for you.”

Alissa looked at me, confusion all over her face. Words weren’t sinking in anymore.

“I j-just wanna go home… Please, P-please...” She cried softly, looking me straight in the eyes. “I-I can’t do it anymore. I feel sick. It hurts…”

I caressed her cheeks, and she let me do it. No grimace, no disgust, no wailing, just begging sad eyes and tears making her eyelashes look even longer, thicker.

“Promise me you will go straight to your room. You’ll do your best so your parents don’t see you like this, and if they do, you’ll come up with something.” I said. “Promise, and I’ll let you go.”

“I promise,” she answered, clumsily standing up. Then while she fixed her dress, she added, “Don’t worry. T-They don’t care about me.”

I put on a robe, and I walked her out. We didn’t exchange any other words. Trembling, she stayed by me and Brandon while Edgar pulled over in front of us.

“See you in two days, Alissa.”

She just looked at me, her face still red and her eyes a little swollen from crying so much in the last an hour or so, then she nodded resignedly.

After the car left, Brandon looked at me, “Everything all right, sir?”

“Everything is perfect, my friend. Just perfect,” I replied, getting back inside the house.

A2O - 2020

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