The Boss - Part 4 "Deep"

Hey, there.

Part 4 - ?Deep?

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 HAVE BEEN WARNED.***

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We went to the top floor of the enormous building located downtown. It was the restaurant of a friend, Michelle. Alissa hasn't looked at my face again since we left the car, after I had abused her delectable mouth and throat. She walked timidly by my side, looking to her feet at every opportunity, ashamed, and probably angry. I liked it.

I looked at our reflection at the elevator, and I liked what I saw. I was wearing one of my favourite blazers, black, with a gray dress shirt underneath, and no tie. I hate ties. Alissa was simply breathtaking on her dark blue strapped dress that hugged her beautiful body, and her perky breasts proudly protruding in their cups. She looked even taller wearing a pair of white heels. Her slender, skinny, silhouette was completely noticeable, and her white skin contrasted with the color of the dress in a spectacular way. Lucky for me, I was even taller, and my body had twice the width of hers, if not more. I loved the way she felt so, so delicate, breakable, standing submissively by my side.

When we got out of the elevator, to the dimly lit hall surrounded by statues and paintings portraying places in Italy, I sent Brandon first. I had to be sure they were ready for us, as I wanted to go straight to our table, located in a separate part of the restaurant, without us being seen. He came back and nodded, then we moved.

The place was roomy, a lot of space between the well arranged tables, and the ambience was cozy and dark, as I liked. Antonio, the maître d', came with Brandon to receive us, which he did in a very excited way. It had been a while since the last time I showed up at that place, or had to use my Italian for anything. He complimented me, and then was extremely courteous to Alissa, and that broke her introspection a bit. At that moment, I saw how empathic she was, and which was probably her charm? And a big problem: it didn?t matter how terrible she felt inside, if somebody talked to her in a nice, warm way, she would reciprocate, no matter what. She was incapable of breaking somebody?s expectations, apparently. This was another indication towards my belief that she would eventually become a very good pet. I just had to give her the attention she needed, and to play her feelings the right way.

Our table was a two seater separated from the rest of the restaurant by a red curtain, and it was a considerably big area fronted by a glass wall that gave us a magnificent view of the city at night. I had the impression that they had set that up specially for me, since another four tables could fit that room easily. Antonio sat Alissa, then me, and he left saying that Michelle was coming to greet me as well. Brandon stood by the curtain to make sure we weren?t seen or interrupted, as he knew he should do.

Before I could talk to Alissa, Michelle walked in, already with his arms open for a hug. He was a big Italian from Rome, with long blonde hair, striped blue and black buttoned down shirt, and very tight black trousers kept in place by a belt with a huge buckle sporting the initials of a famous fashion brand. He could be easily mistaken by a woman on the street, if seen from afar.

When I stood up, Alissa did the same, which surprised me. Yet another proof that she cared, no matter what was happening. What a good young slave I got for myself, I thought. We greeted each other, then Michelle went to Alissa and kissed both her cheeks like she was an old acquaintance of his. He looked her up and down, and looked stunned.

?What a beautiful, beautiful lady you have here!? He exclaimed, his Italian accent as evident as ever.

?Thank you.? She replied coily, blushing, trying to keep composure.

?Yes, I know. This night is hers, so lets treat her well,? I said, and she looked at me puzzled.

?Be sure we will, amico mio. I have that Masseto Toscana that you like, should we start with that and aperitivi??

?Yes. That sounds good. Thanks for receiving me brilliantly like this on such short notice, my friend.?

?For you, always. Ci vediamo tra poco! Enjoy your evening.? He acquiesced to me, then to her, and he left.

The night went on pretty smoothly. Apart from the fact I had to demand that she drink wine with me, after she insisted it wasn?t a good idea, that her parents could be upset, or suspect of something. I had to remind her that ?they didn?t care about her.? After that, she was fine. After the alcohol kicked in, she looked less nervous, more open for casual conversation. We ate delicious food, which I made sure to be as light as possible because I had plans for the rest of the night.

Then, after dinner and still drinking, I went to action.

?Alissa, I?m going to call somebody, and I want you to listen.?

She looked at me, intrigued, while I took the secure phone out of my pocket and dialed a number. After the person on the other side of the line picked up, this is what she heard:

?Hi, Ashley.?

Alissa?s eyes widened, and she almost dropped her glass of wine.

?You don?t know me, but I?m calling you for a special reason. You see, I have very important information on you, and if you hang up I?ll make sure it is all over the internet. Your school, your friends, and especially your parents, they will all know.?

?

?Wow, what a dirty mouth you have. So, should I just go for it??

?

?That?s a good girl. Smart of you, to shut up and listen, because it is not only about your beautiful sex videos? I know about Jameson as well.?

The line went silent for a while, and Alissa got pale in front of me. For a moment, I thought she would throw up.

?What do I want? I?ll tell you soon as we can meet in person. I?ll text you the address. Just so you know, this phone is untraceable. Even if it wasn?t, I have contacts within all scales of the judiciary system, and the police. Let?s avoid you being called an incestuous little whore, losing your scholarship, your parents losing their jobs at school? You have a lot to lose, and to gain, with this. So, just follow my instructions and everything is going to be just fine.?

?

?No, I will fuck you. Very soon. Remember, one word to anyone, and I?ll know. Have a good night.?

I hung up. Alissa was breathing hard through her mouth, pale, a face full of confusion and incredulity.

?How do you feel about that?? I asked. But she couldn?t say anything, so I followed my plan. ?Did you know that she was the one who told everybody what you said to ?Jamie? on your first night together? This is why your little best friend didn?t stand by you back then, because she was the one who made your life miserable. Ashley and Jameson have a thing going on. I mean, they had, as I?ll make sure that is over.?

?This can?t be true?? She said, tears forming in her eyes, she looked sick.

?You, more than anybody, know I can get whatever information I want. Perks of owning one of the biggest communication companies on the globe. I mean, that and a friend who can use my resources.? I said, and she looked to the side, propping her elbow on the table, her face on her hand. I asked again, ?How do you feel about that??

Alissa inhaled deeply, ?T-That WHORE!? She vociferated, crying.

?That?s my girl. I think you agree with me that she deserves to be hurt, don?t you??

She looked at me, anger and confusion on her beautiful black eyes.

?I mean, you were always the good girl, and look where it took you? Here. With me. Don?t you think she deserves the same? Maybe worse?? I asked.

?She does... She does!? Alissa said in a low voice at first, still confused, then repeated it like she meant it.

Out of the blue, I called Brandon out loud, startling her. When he showed up, I asked him to close the curtains and ask the restaurant staff for some privacy. He nodded, closed the heavy red curtains, and left. She looked at me in a puzzled way, until I talked again.

?Now that I?ll have you both, and that I?m doing this for you, you have to be sure you stay as my favorite?, I said while gesturing with my finger for her to come to me.

Alissa inhaled deeply, but stood up readily.

I pointed to my side, and when she got there I said, ?Take off your panties.?

Looking me in the eyes, the young girl reached under the hem of her dress, and she pulled down the black lace panties that she wore, slipping them off one heeled feet, then the other, and placing the underwear on the table. I moved to the edge of my seat, grabbed her by the waist, and I made her straddle me at the same time I opened the zipper on my pants and freed my cock, absolutely erect, pulsating. Her hair fell from the sides of her hair, veiling her face and mine, our foreheads touching.

?You are a good girl, aren?t you?? I asked while rubbing the tip of my dick on her still dry pussy, to then feel it getting moist soon as I slipped in between her mounds.

Alissa gasped, closing her eyes, ?Yes.?

?Do you want me to punish her?? I said, pushing her down, the big head of my cock forcing passage through her tight entrance, then sliding in, with what felt like a pop.

?Ohh?? She groaned and winced, then she said, ?Y-Yes.?

I grabbed her tight little butt with both hands, moved her up a little bit, then I fiercely forced her down again. I felt a good two inches, maybe more, slid into her warm, inviting insides. She groaned, loudly. The girl was unbelievably tight, just like the two other times I had experienced her before. I was glad. It wasn?t the situation, it wasn?t the fact that she had had sex only once before, it was her. She was that tight. I grinned maliciously, and I started to voraciously move her up and down, fucking her teenage pussy, pushing more and more of my 9 inches (23cm) dick inside of her.

Alissa?s slender legs trembled hardly, while the girl moaned, groaned, and gasped furiously. She was also getting wetter by the time, letting me go deeper inside of her more easily. Soon, as was humping her roughly, big movements up and down, and she wrapped her arms around my neck.

?AUGH!? She whimpered loudly on my ear when, finally, I felt my cock reaching her deepest part, which felt amazing. It felt like her body enveloped me as a whole inside of her, while it stretched her, painfully. Even so, she didn?t complain, not a single no, just desperate groans and whimpers, ?AUGH! A-AH! O-OUCH! GA-AH-AH-AHH!?

She burst to tears when the thrusting got too frantic, almost the entirety of my rod going in and out of her vandalized cunt, and I was in heaven.

Then, I stopped. I had learned my lesson. I didn?t want this to end so quickly.

I unwrapped her arms from around my neck, and I sat her upright on top of me. Alissa propped herself on both my knees, behind her, leaning back a little and arching her back in a beautiful way. She just looked at me, her hair falling sideways like a black, lustrous curtain, covering half of her gorgeous face. Tears ran down her high cheeks, dripping from the edges of the beautiful straight lines of her jaw and chin. Her legs shook, tense, with the effort she had at that position not to be impaled by my long, thick member. I took my time sliding down the straps of her dress, pulling it down until her marvelous young breasts, with those light pink and delicate nipples, stood proudly in front of me. In that position they were perkier than ever. I started nibbling at her tits first, then I started biting them.

?Augh? AUGH!? She cried, her arms shaking, and the intensity of her groans varying accordingly to how hard I bit her. ?UUUNGH! GUUUUH!? They just got louder as I started to bite and pull at her sensitive nipples. ?GUUUUUUUH! UUUUUUGH! M-MY B-BREASTS! AAAAUGH!?

?I?m just leaving some marks in here, so you can remember me tomorrow,? I said, then bit her hard yet again, on the lower part of her left breast, to which she groaned again, loudly as ever. ?Nobody is going to see this, just me, so don?t you worry about the purples tomorrow.?

I kept torturing her like that for more than a minute, and I noticed her love canal twitching every time I did so. It was lovely.

?Would you like me to stop,? I played with her, an eyebrow up.

?Y-Yes,? she whimpered.

?I?ll let go of your titties, but before we finish, I want you to let yourself down on me, until all of me is filling all of you.?

Her eyes widened. She took some seconds to understand what I said, her full lips trembling.

?Come on, let go of your arms, let yourself go down until it is all inside of you,? I instructed.

Alissa was panting loudly, her chest heaving, while she moved her hands from my knees to my shoulders, her legs straining to keep her up. Slowly, she let her weight down, little by little, impaling herself on my dick. It was fine for the first two thirds of it, then after just a little more disappeared in, I felt its head pressing against her cervix, making her groan.

The girl looked me in the eyes, terrified. ?Go on, sweetheart. Let yourself go. I know you want it.?

Alissa then gritted her teeth, while she relaxed her legs and let her weight do the job. Suddenly, I grabbed her by the back of her knees with my both hands, taking her feet out of the floor, and making her fall on my dick. Two of the three inches that were still out of her were forced in, the head of my cock thrusting its way up, stretching her tight pussy and pushing up hard against her womb.

?GUAAAAAAAAHHHHHHHH! N-NOO! NOOOO!? She pleaded, but I let go of her legs, while she shook her head desperately, I wrapped my arms around her arms and torso, and I pushed her down. ?YAAAAAAUGHHHHHHH!!?

I felt myself going in, inch by inch, her insides twitching, until there was nothing left out of it. The girl trashed, screamed, howled, which just increased after I started moving inside of her, pushing her up and down with my arms. I couldn?t move much in that position, but her pussy squeezed the entirety of my dick so much, and its head grazing forcefully on her cervix felt so good, that she was getting me ready to burst my cum inside of her at any moment.

?AAAAAAAUGH! N-NO! NOO! TAKE IT OFF! TAKE IT OFF PLEASE! IT H-HURTS! IT HUUUURTS!? She trashed violently, crying desperately and begging for me to stop crushing her womb with my dick.

I grunted, pushing myself in and out, barely aware of Brandon?s voice at the other side of the curtain while he pushed away someone who came to check on us after hearing her screams.

?That?s it, sweetheart. Take it! TAKE IT!? I roared as I felt myself gushing load after load of my cum directly on her womb, forced all the way up by my massive cock.

?GUUUAAAAAAAHHH! G-GUUUHHHH!!? Taken completely by the pain, but her young pussy as wet as never before - being it by her juices alone or her blood - she just bent her head back and howled with every ounce of air her lungs had while I poured everything I had in the deepest part of that gorgeous young girl.

After I finished, I breathed hard, savouring it. I hadn?t even noticed that Alissa didn't react anymore. She just stood there, on top of me, little convulsive motions around her whole body, looking at me, but with a lost gaze. The girl just moaned softly, her breathing erratic, while my member was still completely buried inside of her.

I put one hand on her cheek, making her look at me. ?Are you there?? But she didn?t answer, just uttered broken, whispery groans. I slapped her face a couple times, lightly. ?Alissa?? I called, and I saw her break from the sexual pain trance I had induced on her and come back to reality, as I saw her eyes focus on mine.

?P-Please? En-nough...? She pleaded, crying.

Then lifted her, slowly, still savoring it as her pussy sucked me, tring to keep me in place. I felt a pool of my cum, stained in red, run down from her pussy and onto my lap. She winced, with gritted teeth, then let out a sharp gasp when it finally popped out of her. I put her sitting on my lap sideways. Her shivers, her soft moans, it was all so enticing that I stayed erect, hard. I could keep fucking her, but I chose not to. She automatically put both hands over her stomach, her womb, and moaned in pain.

I brushed her hair behind her ears and out of her face. Then, I leaned forward and kissed her lips, which she tried to avoid at first, as if she was in shock, but when I pressed my lips against hers again she kissed me back.

?I punished you, now I?ll take care of you,? I said caressing her cheeks. ?You don?t have to worry about a single thing in this world anymore, as long as you?re mine.?

Alissa looked at me, deeply, as if she had realized something, but she didn?t say anything. Instead, she laid her head on my shoulder, still convulsing, moaning.

I just ran my hands all over her, caressing her, feeling her breath go back to normal and the spasms lessen. I had a huge and satisfied grin on my face. I never thought something like this could ever happen. I would keep abusing her, fucking her, sexually torturing her, until she forgot what normality was. Then, I would still have Ashley to play with. I won.

Then she murmured something I couldn?t understand.

?What is it, sweetheart??

?I want her to suffer. More than me.?

"Oh, sweetheart. Don't worry. What I have planned for her will make what we have look like a fairy tale."

A2O - 2020

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