Anna is a strikingly beautiful and scary rich Russian socialite who some call Russia’s Paris Hilton. She is about to get $50 million dollars richer as a result of a very wise investment in New York, and she is already a millionaire heiress. Anna has one of the most desirable penthouse homes in New York City, at the top of the Time Warner building with gorgeous vista views of the entire city and harbor. The home was designed by famed architect and designer Noel Jeffrey. She bought the home about 8 years ago for less than $10 million, so that will be quite a healthy profit. Anna’s bank account is already healthy. She is the daughter of a Russian billionaire named Vasily Anisimov who is on the Forbes list of wealthiest men in the world, although his vast wealth has reportedly declined in recent years.
Anna's encounter starts when she wrote me an email. I wrote her back instantly. Then I called her. I invited her to fly from New York to Dallas to " Let me dry rape her asshole" as I put it. Hearing those words made her so fucking wet. She is conflicted, she knows I'm an evil asshole. But I'm so rugged looking ( think Danny Trejo). Anna has never been with someone that can do what she needs. Not only can I do it, but I like the whole game as much as she does. We had phone sex a few times. I'm very graphic. Telling her that as soon as I walk in, I'm going to bend her over and rape her asshole dry with my monster cock. That it won't be for her pleasure at all. That I'll just use her for myself.
Finally Anna agrees. She will definitely come. She calls me when she's close. I warn her not to lube herself, or else she would really suffer. When she rings the doorbell, her heart jumps into her throat. Her stomach feels like it is doing back flips. Anna is so nervous... I open the door, and she walks in. Reality is different from my own predictions. We chat a bit. Sit down. Watch tv. I sit close to her, I put my arm around her shoulders, it starts - I start kissing her. She smells so good. Tastes fucking great. I'm fingering her. She tells me we should go to the bedroom. She follows close behind me, I'm pulling my shirt off as we go. I strip her. She feels strange to be naked, while I'm fully clothed. I'm fingering her harder. Shoving two of my dry fingers into her asshole immediately. It burns. Anna is trying to pull away from me. I turn her around, pushing her down on the bed, with her feet still on the floor. I'm hissing into her ear " this is what I have been waiting 3 hours to do, you fucking slut." Anna starts to panic a little. She feels my hard thick, hot, dry cock trying to force its way into her little tight asshole. It's a scary feeling.
Anna tries to turn around, but I'm pushing her shoulders down, keeping her in place, pressing into her. She feels the head of my fat, dry cock searing into her little hole. She is just reacting now. She knows this is what she has always wanted, but the reality isn't quiet matching up to her fantasies. The last couple times I had done this to her, it hadn't hurt this bad. Anna again tries to pull away from me. The burning pain in her asshole is intense. Anna begging me to stop. She presses her hips into the bed as hard as she can, tightening her asshole as much as she can so I won't be able to go in anymore. I try a few extremely painful jabs to get in, but with the friction, and the position we're in, I stop. Anna is hoping I'd let her have a break. Give her some kisses. Make her pussy a little wet, and use the lube to soften things up a bit... but that's not the case.
I push her up on the bed fully, on her stomach, flat on the bed. I spread her legs roughly with my knees. By this time, I have taken off my clothes. Anna feels my skin on her back. My mouth at her right ear. Whispering nasty words to her. Telling her I'm going to make her bleed. Telling her this is what getting her asshole raped feels like. The way she is writing, it may seem like it took me some time to reintroduce my fat cock to her tender asshole, it is only moments. Moments until I'm able to forcefully, and slowly... with agonizingly unmerciful thrusts, sink my hard, dry flesh into her asshole... telling her the whole time, that this is why she flew 3 hours to have done. To rape her asshole dry. " This is what getting your asshole raped feels like."
Telling her that I'm making her my Russian whore. Telling her that I'm going to use her to get out all of my frustrations. Her arm is caught under her in an uncomfortable angle, She tries to pull it out, but I push her harder into the bed, using my forearm on her shoulder blades to pin her down, while I use, short, hard jabs to go deeper into her burning hole. " John, John please...wait. Just wait a second. Let me try to get used it," She begs. " Please John... omg, it hurts so much. It's burning. You're hurting me....." " That's right. I'm going to hurt you. Like I told you, you're going to bleed tonight. I'm going to rip you a new asshole. It's going to take you a month to get over this." All the while I'm fucking her hard. Anna has been fucked up the ass before, but she always got use to the pain after a few thrusts. She is thinking this is going to happen this time too. That she can ride out the painful part. That it'll be over soon. Maybe it is because she is so dry. Maybe it is because of the angle. Maybe it is because I'd already torn her with my first violent thrust, but the pain never ebbed.
My thrusts are rough and hard. They weren't all the way in, and all the way out - they went from deep to deeper. Short jabs that didn't slide in and out of her. Too much friction causing the burning and intense pain she thinks. It is more like with every thrust, I'm churning her asshole in and out. Like the sides of her asshole are stuck to my dry, thrusting cock, and I was just going to turn her inside out if I pulled out all the way. She feels the plunging effect in her stomach. Anna starts pleading with me to stop... my face is so close to hers. She turns her head, calling my name..... telling me she meant it. " I mean it John, I really mean it... please, just stop for a minute. You're really hurting me." Anna knows the panic is in her voice. I said I know. " I know you mean it. I love to hear you beg." I keep fucking her harder. I wrap my hand around her neck, she had managed to pull her arm free during the ordeal. All that did is allow me to reach under her, and squeeze her tit hard.
It's hard to describe how she feels at the moment. I'm choking her a little, I'm squeezing her tit hard. And fucking her asshole harder, she knew she is bleeding. Anna feels overwhelmed, and a little nauseous from my intense thrusting. All of a sudden, I pull out. And laid down next to her. Anna still feels me in her asshole. It feels like it is on FIRE. Red hot. Burning, and it feels open, and full at the same time. The pain isn't deep though. I hadn't gone in all the way. I had concentrated on hurting the first 1/3 of her tunnel. I said she had taken it like a good girl. Anna is lying there in the same spot, on her stomach, trying to calm down. She is shaking from head to toe. Her legs are like rubber. I wash my cock, and got back into bed. Anna guesses she should have gotten up to clean herself a little too, she couldn't get up. She is too weak from being attacked like that. We kiss. We ended up with her on top. Kissing. I gave her a few moments to grow accustom to my length and my girth, moments which are spent looking into her eyes triumphantly. When I thought she was ready I draw back, feeling her cunt clinging tightly to me as if it is reluctant to let me out. Only the tip remained in her, then I slammed into her, spearing her, impaling her on my long thick pole, thrusting in hard, hard enough for her to feel it throughout her body.
" Fuck!" Anna shrieked. She is torn between wanting to tell me to slow down and wanting to demand that I fuck her harder. But it is moot; all she can do is unleash a stream of profanity. " You big-dicked mother-fucker! You're gonna fucking break me!" Her words affected me like spurs on a horse. I give a low growl and started to fuck her harder. I feel her cunt rippling around me, convulsing continuously, as if she wanted to milk me. I'm far from done. I drive into her a few more times, putting my legs into it, ensuring that she'd feel each powerful thrust. Then, still lodged deep in her, I grab her hair pulling her up, rolling as I did so she wound up on top of me, facing me. She screams, in pain, in surprise—and in pleasure, and her weight bore down on my shaft and a sudden ecstatic flash burns through her.
For a moment, Anna thought I wanted her to take control, that proved to be a mistake. What I wanted, rather, is to show off. My hips bucked, and I took her by the waist, lifting her up before slamming her back down, easily manhandling her as I used her like a living sex toy. The muscles in my arms and chest gleamed in the dim light of the bedroom as I broke a sweat. Anna's tits bouncing wildly as I hauled her up and down my length. Her hands went to her chest, steadying them, and giving her a chance to cup squeeze her firm breasts, to tweak and pinch her nipples. She is screaming short staccato screams, and she dimly realizes that it is her. Her voice is a bit hoarse, and her cries of pleasure are interrupted by the way my powerful thrusts drive the air from her lungs. She tries to start bouncing in rhythm with me, but my relentless strength simply overpowers her, making her into a true fuck-toy. She is grinding her hips into my lap. Trying to get my cock as deep as she can into her pussy. Kissing me. Sucking on my lips. Kissing my neck, and ears. Grinding her wet pussy down on my hard cock. Trying to get it up into her cervix.
Then I tell her to get off. That I wasn't done with her asshole yet. She clutches me tightly. Placing her head in the crook of my neck. " Please no John. No more. I can't." She tries to persuade me by grinding down harder. " Please John, just fuck my pussy a little longer." She is thinking she can maybe get me to cum... saving herself from more hurt. Testing me really. Testing to see if I'll cave. I pushed her off roughly. Telling her that it's no use. That I'm going to fuck her asshole again and again. She tries to lie on her back, we struggle a little while... but I'm to strong. She ends up on her stomach again. Anna feels my cock at her asshole instantly. She feels that thick, burning, scraping again. I say, " this time I'm going to show you how big it really is." Anna didn't know exactly what I meant, but it didn't take her long to figure it out. I'm going in much deeper this time. And angling my fuck stick so that it is scraping the top of her asshole more than the bottom. I start thrusting into her fast and hard. Deeper in and out than the last time.
I said, " fucking you hard is a pleasure." Anna is whimpering, telling me it hurt. Telling me it burns. Telling me it hurt deep inside. I'm making her stomach cramp a little from the pressure I'm causing to build up in her from my angled thrusting. I push in hard. M shaft scraping her soft tissue on the inside, and on the top of her asshole. He said, "when you bleed, remember this" as he really scraped up and deep into my hole. It was like razor blades up my asshole. The pain was so intense. He had his hand wrapped around neck again. I was holding onto his hand. Trying to actually get him to squeeze harder. Anna doesn't know what happened first at this point..... she can't remember whether I said it, or did it first... she guesses it is like at the same time... I said, " I'm going in deeper," and she feels my fat cock go to a deeper place inside her. Anna feels my fat cock pass a point inside her where the flesh seems to be thinner and more sensitive. Anna feels it as soon as I said it. I had just done it. I had decided that I'm going to drive my cock deeper into her, and I did it.... didn't ask her permission. Just told her, and did it. She feels it. It is indescribable. Then feeling me thrusting so deep in her. It made her groan as soon as I did it. She feels it immediately.
Then I fucked her harder and deeper. Fucking her flat into the bed. Each stroke fucking her harder and deeper. It never stops hurting. It never got better. It just keeps hurting.... while I choked her a little more. Telling her " She is my Russian fuck whore." That if she lived closer to me, that I'd never masturbate again... that I'd use her to cum four or five times everyday. That I'd never let her asshole heal. That it would always be my gaping, raw, sore fuck hole to use and abuse. Telling her how hot and tight she is. Grunting as I drive it home again and again. So deep that she can feel it giving her cramps again . My cock is in so deep in her ass. Anna loves the way I talk. It makes everything so much more visceral. She doesn't know how long I fucked her, probably another 20 minutes. 20 minutes of agonizing, raw, hard, deep anal plunging. Anna isn't dry anymore... but she is so raw, that it feels like someone is shoving a red hot poker in her asshole - one of those iron fireplace pokers that had been heated until it is bright red. That's what it feels like.....
" John, John pleeeeeeeeeease...." Anna starts begging me. She needed something else. Needed more. Needed a break.
She thinks I can tell she is about to break, I pull out suddenly again, telling her, she has been such a good girl. Taking her ass rape so good. That I'm going to give her another treat. She has been waiting for this. I flip her onto her back, and went in.... as soon as she feels my tongue on her clit, her eyes rolled back into her head. She would like to lie, and say I made her cum, but I didn't. Anna feels rushed. Like I wanted her to cum in 5 minutes. She needs more time. It feels so good. Anna holds my head down there for a while. Then I fucked her pussy again. While she is on her back, with her legs over my shoulders. I squeeze her breasts... driving my cock deep into her like a drill.
Anna thought I was going to cum like that, but she should have known better. She feels my hands on the back of her knees.... I lift her hips up off the bed, and I slam my cock into her asshole in one swift, hard, deeply penetrating thrust. At that angle, it is like her asshole is closed up. I push her legs closer into her chest, and start pumping away like a piston. Fucking her hard. In and out, in and out. All the way in to the hilt, then all the way out.... it feels wet, and her asshole is stretched open again, but she is also very raw, and sore... so it burns. I'm hitting new spots that hadn't been ravaged yet.... feeling more areas of her inner flesh being abused made her want to cry out of helplessness....
I keep right on going...fucking her so hard at the end. She feels my cock swelling bigger in her asshole, she knew I'm about to cum. Anna holds on while I fuck her torn, sore, abused asshole to oblivion. Anna feels my cum shoot up into her... it actually made things feels better. The hot, wetness is a relief. I didn't pull out... I hold her like that. With her legs pressed into her chest... my cock lodged all the way into her asshole... until I had spewed all my cum deep up into her asshole. Then I slowly pull out. Anna feels my cum ooze out when I pop my fat cock out of her. Anna ran to the bathroom. Anna feels my cum seeping out of her burning asshole. I sat there, with her legs shaking, her hands over her face... trying to contemplate what she had done.
Anna took a quick shower. Barely able to stand up. She got back into bed with me. We slept until I got up and showered. Since she lives so far away, a "relationship" was never a possibility. Not to mention the fact that I'm an evil, asshole. I'm not worthy of her. Anna knows that sounds conceited, but it's true. My God can I FUCK. She had been fantasizing about that night for months now. Every time she thinks about when I said, " I'm going in deeper," and then she felt it at the same time... Felt it pass into that deeper part, through a deeper, angled, crevice into another part of her body, it makes her horny all over again. Anna had never meet a man with a darker side the hers. This encounter scared her, she had never experienced a monster cock before and had never endured a fucking so rough and long. Anna is in conflict now, will there be a next time with me or is this the only time she will see me. After all, John really isn't worthy. But John sure knows how to fuck a girl into oblivion. I'm right, it will take her a month to get over it.