Monday, October 29, 2012

Shame - Chapter One


Warning: The following story describes events that are illegal, immoral, and just generally a very, very bad idea. Nothing in this story should be emulated. Nothing in it is a good idea. Nothing in it actually happened, either -- it's a work of pure fiction. If you are underage, easily offended by things that probably should offend you, or unable to differentiate between fantasy and reality, you should probably piss off right now.


Alexa had no idea how attractive she was. She could have easily been a model – or a porn star, if she chose to go that direction instead. Like many women, though, Alexa suffered from extremely low self-esteem. Having been chubby as a child she still saw herself as morbidly obese, despite the fact that she was at the very bottom end of her ideal weight range. Too many South Park inspired jokes had convinced her that her bright red hair and freckles were marks of shame. A culture that insists that our character is based on our appearance had made her believe that her feline face wasn’t attractive – it was bitchy. When she looked in the mirror, she saw a very different person than what I think the rest of the world saw.

I realize that I sound a bit hypocritical here, criticizing a culture that assigns value and characteristics based off of physical appearance when a lot of my initial attraction to her was purely physical. I’ll admit it – I can be shallow at times. For whatever it’s worth, though, I was attracted to her personality as well – or at least what I assumed her personality was based on the things that she’d say. The embarrassing truth is that I knew about her long before she even knew I existed.

Despite her skewed self-image Alexa frequently posted nude pictures of herself to the Internet, which is how I found her in the first place. I’m sure most people thought she was just fishing for compliments in the hopes that countless strangers telling her how ridiculously hot she was would make her feel better, but I wasn’t so sure. There might have been some truth to it – I think everyone likes being told they’re attractive from time to time – but something about the comments she’d make led me to suspect that she wasn’t really looking for compliments at all. I can’t put my finger on what it was, but I always felt like a part of her yearned for harsher criticism instead of blind praise.

It took me a lot of time and alcohol to work up the courage that I needed send her a message. I’m really not normally shy around women, but she had a massive following. Every time I thought about saying something to her a little voice in my head reminded me that there were probably hundreds, if not thousands of guys talking to her at the same time; many of whom were probably saying more interesting things than me. I felt like I needed something to really stand out, but I couldn’t figure out what the hell I could say.

I wish I could claim that I figured out some magically clever thing to say which won her heart, but that’s not the truth. The truth is that the message I ultimately sent her was painfully bland; free of anything that I feared she might deem creepy. I expressed no sexual interest, no desire, and nothing even remotely personal. I told myself that I had to do it like that because I didn’t want to blend in with the countless other men telling her how beautiful she was and I certainly didn’t want her to think I was some kind of a pervert, but I don’t think that was my real reason. I think on a subconscious level I intentionally sent her a boring message that she’d be unlikely to respond to or even notice just so I could feel like I made an attempt and move on with my life. After proofreading it for the hundredth time I clicked send, reminded myself not to get my hopes up, and went to sleep.

I woke up the next morning with one of the worst hangovers of my life. Turning on my computer, I reminded myself that the odds of her responding to my message were practically zero and that I shouldn’t get my hopes up. I wanted to take a piss and a shower, but I couldn’t seem to pull myself away from my computer until I saw for a fact that my inbox was as empty as I expected. As it slowly booted up, I tapped my foot impatiently.

After what felt like an eternity my browser finally opened. To my surprise, there was a single (1) next to my inbox, indicating that someone had sent me a message. As I clicked the icon of an envelope I reminded myself that it obviously wasn’t her, and I was an idiot to get excited over what would almost certainly turn out to be a random piece of spam. Even when I saw her username in the From: field I just couldn’t believe that she had actually responded to me.

Nervously, I read over her message. It was short and just as impersonal and asexual as the one that I had sent her, but I couldn’t care less. I hadn’t expected any reply at all; I wasn’t about to be disappointed by the fact that she hadn’t exactly demanded to have sex with me. I was just happy that I had an opening. After typing out a quick, slightly less impersonal reply, I hit the bathroom.

Over the next few months our relationship progressed – kind of. We got to know each other, talked on Skype, and became friends. Unfortunately, that’s all we became. I was too afraid of scaring her off to push for anything more, and she seemed completely oblivious to how attracted to her I really was. I was torn – I loved talking to her, but it hurt me to be constantly reminded of the fact that she simply did not see me in any way that was remotely sexual.

On the bright side, I wasn’t the only one that she didn’t realize was interested in her. Alexa was actually still a virgin, though it wasn’t by choice. I was surprised when she first told me, though it made sense when I thought about it. If she hadn’t noticed how much I desperately wanted her then it was likely that she hadn’t noticed how much others wanted her, too. There was also the issue of her looks – her beauty was extremely intimidating; I could see how men would be too afraid to approach her.

We talked about sex a lot. Despite having never actually had it, she had a ridiculously high sex drive – and I never passed up an opportunity to discuss it with her. I knew that I shouldn’t have, I knew it would only hurt me, but I couldn’t seem to stop myself. I felt tremendously creepy, but I loved hearing about her sexual fantasies, most of which involved being dominated and humiliated. It killed me that she only told me because she apparently thought I was a eunuch and therefor safe, but I was willing to accept that pain just to find out more about her. She told me everything, even the fact that despite masturbating constantly she had never actually reached orgasm. I listened eagerly to every word, only to secretly jerk off later while thinking about the things that she had said. I felt like a total pervert, but I couldn’t help myself.

The worst, though, was talking to her about her attempts to acquire a boyfriend. Hearing about her sexual thoughts was painful and enjoyable at the same time, but hearing about the men who weren’t me that she wanted was pure torture. She’d whine constantly about how all of the men she was attracted to didn’t seem to even know she existed, leaving me wanting to choke her. If I hadn’t been so tremendously frustrated I might have appreciated the ironic humor of the situation, but in my state it took all of my willpower just to restrain myself from saying something regrettable.

Still, I managed. She’d complain that she felt like she was unattractive, I’d tell her that was ridiculous and remind her how beautiful she really was. She’d tell me that she felt fat; I’d tell her that her body was perfect. I became her cheerleader, constantly building up her self-esteem only so that she’d be able to try again with someone else who wasn’t me. Every time I consoled her I could feel a part of my soul was being painfully ripped away, but I forced myself to hide it. I did truly value our friendship and I wanted her to be happy, but it was killing me that she couldn’t see how I really felt about her.

As time progressed I found myself getting more and more bitter. It was difficult for me to believe that she couldn’t really see how I felt about her, yet the alternative was also tough to swallow. Alexa never struck me as the sadistic type, and it didn’t seem likely that she’d be using my attraction towards her as a way of controlling me, but I couldn’t see how else she could be so oblivious. I found myself growing deeply resentful when she told me about the men she was attracted to; it was a constant struggle just to avoid screaming at her for not giving me a chance.

It was about six months after we had first started talking that I finally lost it. We were talking about her most recent unrequited crush and how she felt like he didn’t even know she existed. This was painful, but hardly abnormal. I told her how she was the most beautiful woman I had ever seen, which I had told her countless times in the past. Normally she’d just shrug it off and continue complaining, but that time she responded in a way I didn’t like.

I know you think that, she sobbed, but you seem to be the only one. No guy that I’m attracted to seems to even notice me; I swear to god I think I’m going to die a virgin. I just don’t see why I can’t find a guy that’s hot who likes me.

I don’t know if it was the casual implication that she wasn’t even remotely attracted to me, the lack of gratitude for my compliment, or just the complete obliviousness to my attraction; but I just couldn’t take it any longer. I consciously knew that every bit of pain that I had experienced in talking to her was my own goddamned fault for putting myself in that situation, but at that moment I felt like she was doing it to me on purpose. I didn’t feel like her friend, I felt like her doormat, and I wasn’t able to tolerate that any longer. I knew it was wrong, but I wanted to make her hurt as much as she had made me hurt.

I can’t believe that they don’t notice you, I shrugged, doing my best to hide my rage. I mean, at your weight I have to think that you’d be pretty hard to miss.

Excuse me? she said, sounding deeply hurt. I knew I should have stopped there, but I was still angry and I needed to vent.

I’m saying the problem isn’t that they don’t notice you," I explained, it’s that they just don’t want you. Look, it’s like this. Say you head down to a farm and see a cow. Just because you don’t fuck the cow doesn’t mean that you didn’t notice that it existed – it just means that you’re not into bestiality. Given that the average cow is both thinner and sexier than you, I think it’s perfectly understandable why they aren’t hitting on you.

I could hardly believe that I had just said such hurtful things, but it was too late to take it back. She had heard what I said clearly, as was evidenced by the betrayed look on her face. I felt terrible, but before I could apologize she disconnected. I tried to reconnect, but unsurprisingly, she declined my call. I had no idea what the healthy thing to do would be in that situation, so I did what seemed like the exact opposite. Emotionally volatile, I grabbed a bottle of vodka and started drinking.

I tried to tell myself that I had done the right thing, and in some ways I believed it. I knew that our relationship was completely unhealthy, and I knew that things would be easier without her constantly occupying my thoughts. I still hated the fact that I had hurt a friend and probably destroyed our friendship, but I knew that I couldn’t continue things the way that they were. As the alcohol started to work through my system, I tried to convince myself that she deserved it for having been so oblivious to my attraction to her, though I couldn’t seem to believe that. It felt important, though – I suspected that I might never speak to her again and I wanted to believe that it somehow wasn’t entirely my fault.

A few hours later my Skype window popped up again. To my surprise, it was Alexa. Unfortunately, after significant drinking I had managed to convince myself that the whole thing was at least mostly her fault, and I no longer wanted to apologize – I wanted to fight. I figured she had only called to tell me to go to hell anyway, so it wasn’t like I would be burning any new bridges. Preparing myself to go for the throat in a futile attempt to save what little dignity I might have had left, I clicked answer.

As her face popped up on the screen, though, I felt myself knocked off balance. I had expected to see her teeth bared and ready to hit back, but that wasn’t what I saw at all. She didn’t look angry, she looked devastated. I could feel my rage slipping away and being replaced by remorse for what I had said.

Okay, before you say anything, she began, I’m sorry. I realize that I was being a total bitch, and I hope that you can forgive me.

I had absolutely no idea how to react. I hadn’t dreamed that she might actually apologize to me and I certainly didn’t have a plan for it. A part of me was thrilled that I apparently hadn’t managed to completely destroy our friendship, but at the same time I couldn’t stand to go back to the way things had been. Emboldened by the alcohol coursing through my veins, I spat out the first idiotic thing that came to my mind.

You should be, I growled. Maybe if you weren’t always such a cunt to me you wouldn’t still be a virgin. We’re only a hundred miles apart, if you had asked me nicely I might have been willing to fuck your fat ass just as a personal favor.

Even as drunk as I was I knew that I shouldn’t have said that, but it was again too late to take back. Surprisingly, though, Alexa again failed to react in the way that I would have anticipated. Rather than being offended, she looked almost intrigued. I told myself that it was just wishful thinking, but it almost looked like she was thinking about asking me nicely.

Worried that I was going to fuck things up beyond repair if I kept talking to her while I was drunk and emotionally erratic, I told her that I had to go and immediately disconnected. It wasn’t the smoothest exit ever, but I didn’t trust myself. I realized that the mere fact that we were still on speaking terms was a small miracle, and I didn’t want to push my luck. After shutting down my computer, I went to bed.

We spoke again the next day, though we didn’t speak about any of the things that I had said. I wasn’t sure if she failed to bring it up out of politeness or out of fear that I’d hurt her again, but I was okay with that. I was ashamed of my actions and I wasn’t eager to discuss them. I wasn’t going to forget what I had said, but I didn’t want to be reminded either. At the same time, though, a part of me enjoyed the feeling of power that I had experienced when I hurt her. I didn’t like that I had made her cry, but for the first time in our relationship I felt like I wasn’t just her bitch.

Over the next few weeks our relationship changed dramatically. I wasn’t intentionally verbally abusive or anything, but I no longer put even the slightest effort into building up her self-esteem. If she hinted that she felt ugly, I’d ignore it instead of rushing to tell her that she was beautiful. Expectedly, it did wonders for my self-esteem. Unexpectedly, Alexa actually seemed to react positively to it as well. Though I couldn’t put my finger on it, it felt like she actually respected me far more than she had before. It felt like she viewed me as a man, rather than some sexless eunuch.

I liked the way that our relationship was going, but I wanted more. Even though I no longer told her how pretty she was I still felt tremendously attracted to her, and I really wanted to move our relationship forward. Complimenting her had gotten me nowhere, so I went in the opposite direction. When she hinted she felt ugly, instead of just shrugging it off I’d agreed with her. I wasn’t outright insulting or anything, but I’d act as if her lack of physical beauty was an obvious fact that she didn’t need to point out. It was a lie, of course – I actually struggled to repress my desire to tell her that I thought she was insanely hot – but she seemed to react favorably to it.

She stopped talking to me about the guys that she had a crush on. At first I thought that was because of what had happened the last time, but as time progressed I began to suspect that wasn’t the only reason. I worried that it was probably just wishful thinking, but something about the way that we interacted made me think that it might have been because I was the guy that she had a crush on. It seemed unlikely, but all of a sudden I felt like I might actually have a chance with her. I knew that I had to do something.

After a week of casually insulting her I made my move. My instinct was to tell her that I was madly in lust with her and wanted nothing more than to move our relationship forward, but I resisted that. By that point I was convinced that Alexa simply didn’t respond well to positive feedback, and though I felt a little uncomfortable about it I couldn’t deny that insulting her actually made me feel good. Rather than plan out some grand romantic gesture I simply got drunk sent her a casual e-mail, doing my best to appear as disinterested as possible.

I have no plans this weekend, I wrote. We’ve been friends for a while, and I’m starting to feel bad for you – the way things are going, it’s looking like you really will never lose your virginity. I’m not crazy about doing it, but if you’re free I’m willing to drive over and throw you a quick pity fuck. Let me know, and no hard feelings if you’d prefer not to. Trust me; I know I can do better.

She replied less than an hour later to tell me that she was free that weekend. Although she technically hadn’t agreed to fuck, I took her willingness to meet in real life to mean that she was interested – after all, it wasn’t like I had concealed my intentions. Feigning more confidence than I was actually feeling, I quickly wrote back to hash out the details.

We agreed to meet up in a motel room near where she lived. Alexa still lived with her parents, so going to her place was out of the question. Taking her back to my place wasn’t out of the question, but I did live two hours from her. Although I didn’t have to worry about explaining my absence to any parental figures, at nineteen years old she didn’t have that luxury. Pissing away four hours for travel time didn’t really make sense. Meeting her for the first time in person in a cheap motel room made me feel extremely sleazy, but it made the most sense. Besides, what I was doing felt already tremendously sleazy – it wasn’t like a change of venue would have made any real difference.

We met up in the lobby of the motel on Saturday afternoon. I’m not generally nervous when meeting someone new, but for whatever reason I felt almost shy. Fortunately, it seemed like she was far more nervous than I was. It made sense, in a way – she was planning to lose her virginity that day, while I had lost mine long before. Either way, I liked it. Her being so nervous made it much less likely that she’d notice how nervous I was feeling.

We headed to our room, talking idly about completely inconsequential matters. Her nervousness was helping me to calm down a lot; by the time that I had closed the door behind us I was feeling pretty confident. She seemed to be calming down as well, though I wasn’t quite sure how I felt about that. I no longer needed her discomfort to relax myself, but I kind of liked her being a little jumpy. In a sick way, the fact that she was so socially uncomfortable around me was sexy – it let me know that she perceived me as a predator, which in turn made it easier for me to act like one. I didn’t want her to have a heart attack or anything, but I wanted to stretch her fear out a little longer.

You can lose your clothes now, I mentioned as I locked the door.

Alexa looked at me quizzically, as if trying to determine how serious I was. Returning her look with one of stern obstinance, I watched as she slowly approached me and reached for my shirt. It wasn’t exactly unexpected. Despite the fact that I had seen images of her naked body countless times in the past, she was alone when they were taken. No longer alone, it was completely understandable that she wouldn’t want to be the only naked person in the room. Unfortunately for her, that was how I wanted it. Grabbing her wrist, I twisted her arm painfully away from my body and slapped her across her face lightly. I didn’t hit her hard enough to actually hurt significantly, but I felt that I had to make it clear that ignoring my orders would not be tolerated.

Don’t make me repeat myself, I warned. I didn’t drive over here to stand around in some shitty motel room and make pointless chit-chat; I came here to fuck your disgusting whore ass. Incidentally, I’m still not even convinced that I want to do that – you looked far more fuckable online than you do in real life. If you want me to have the dishonor of being the guy to finally take your virginity, you’re going to have to prove to me that you’re at least capable of obeying a simple command. Got it, bitch?

I was a little worried that I had pushed too far too quickly. I’m sure Alexa had expected me to be cruel from the tone of our recent conversations, but she looked almost terrified. I liked the fear, but I didn’t want her to be too afraid to actually do anything. Fortunately, she managed to get over it. Still timid and nervous, she began to slowly strip out of her clothes. I was glad to see that I hadn’t scared her off, but I wanted to push her a little bit harder just to see how she’d react.

Should I come back in a couple hours? I asked. I only ask because at this rate, that’s about how long I could see it taking before you’re actually naked. I’ll tell you, bitch – I’m beginning to think you don’t want me to fuck you. If that’s the case, that’s cool – it’s not like I can’t do better, anyway. If I’m wrong, though, I strongly suggest you get your whore ass moving and lose the clothes before you bore me to death.

Alexa looked surprisingly worried. I thought for sure that she’d know I was bluffing – I didn’t drive two hours only to go back home and jerk off – but she seemed to actually buy into it. Moving quickly, she stripped down to her bra and panties. Shooting me a pleading look, she begged me with her eyes to let her keep her underwear on or at least get naked myself so that she wouldn’t feel so awkward. It was a fair desire, but I didn’t feel like being fair. Letting out an exasperated sigh, I conveyed to her that she was testing patience that I did not possess. With a defeated look on her face, Alexa stripped out of the flimsy cotton garments.

It wasn’t like I had never seen her nude before, but seeing her in person was an entirely different experience. I don’t know if her camera was shitty or it was just a subconscious realization that I could actually do something this time, but she looked about a billion times hotter standing there in the flesh than she ever had when she was just an image on my computer screen. My instinct was to tell her that, but I repressed it. Alexa didn’t need another guy telling her how beautiful she was and I didn’t want to risk going back to our old relationship dynamic. Fighting back my instinct, I did my best to feign a look of quiet disgust.

Jesus, I sighed. I can’t believe that I drove all the way down her for this. I mean, I could have just sat around at home jerking off to pictures of dead pigs and saved some gas money. I’m not even sure I’ll be able to get it up now that I see you in person.

I studied her face carefully. I’m sure she felt extremely vulnerable standing naked before me, and I had just flat-out insulted her appearance. Fortunately, she seemed to enjoy it on some level at least. Though she looked completely mortified and afraid, she also looked fairly aroused. On a personal level, I enjoyed insulting her far more than I would have expected to. I know it’s petty, but I was still angry at her for the six months that I spent being her doormat and I was getting off on punishing her for that. Wanting to push further, I took a marker out of my pocket and approached her.

Take your tits for example, I explained, drawing large black X’s along her breasts. You claimed to be a C-cup. Either you’re lying, or you desperately need to get fitted for a new bra. I wouldn’t waste the time or money, though – I don’t think they make bras with cup sizes small enough for those mosquito bites. Just the same, I have to admit that I’m a little impressed – I’ve never seen titties that small sag so much. It almost seems like it should be physically impossible, yet here they are.

I was completely and utterly full of shit. While I don’t know if a C-cup would have been her exact size, it seemed like it would be close enough. It didn’t really matter anyway; while I appreciate large breasts anything larger than what she had would have looked ridiculous on her body. The claims that they were sagging were also laughable – I had been with women who had implants that sagged more than Alexa’s breasts. Still, she seemed to buy it. I don’t know if it was her self-esteem issues, the fact that I was probably playing directly into her unspoken fantasies, or just fear of pissing me off; but she offered no argument.

I’m sorry? she offered timidly.

I’m not done, I replied harshly, slapping her ass hard to let her know that she shouldn’t interrupt me.

Taking the marker, I then drew a large circle around her stomach. In reality it was almost concave; there was practically no fat to be found anywhere. I didn’t really care, though. She hadn’t called me out on my bullshit with her tits; I suspected she wouldn’t call me out on other bullshit either.

Your gut, I continued, might be the problem. Perhaps your tits are seeing how it sags over your waist and attempting to emulate that. God, it’s really unfortunate that we can’t move the fat in your massive belly into your tits – you’d be an F-cup at least. Sure, they’d probably still sag like a cow’s udders, but hey – at least you wouldn’t be mistaken for a twelve year old boy.

Alexa’s facial expression was complex. She looked simultaneously humiliated, terrified, and turned on. It was the reaction that I hoping for, but I wanted more. Spinning her around, I defaced her ass with the marker, commenting the entire time about how fat and disgusting it was. Focusing on her face, I made numerous marks around her cheeks while spouting whatever bullshit I could think of as to how she was absolutely hideous. I didn’t believe a word of what I was saying, but it didn’t really matter – her reaction said that it was working.

Having made my marks all over her body, I wrote the phrase FAT PIG in large letters across her forehead. It bothered me that she wouldn’t be able to see it, so I wrote UGLY WHORE in larger letters on her chest immediately above her tits. I liked the reaction that I got when she looked down and saw that, so I continued. I covered nearly all of her body with degrading phrases, all focused on how worthless, ugly, and cheap she was.

By the time I was finished there wasn’t a single square inch of Alexa’s skin that didn’t have some ink on it and she had begun to softly cry. I felt a tiny pang of guilt, but I reminded myself of all how shitty she had made me feel back when I was telling her that she was beautiful. Besides, it looked like she was enjoying it on some level. It wasn’t just the skin beneath her eyes that was getting damp; I could plainly see her inner thighs beginning to glisten as her pussy grew wet. She might have been emotionally traumatized, but she was also extremely turned on. Noticing that I had noticed how aroused she was, Alexa began to blush in embarrassment.

God, your cunt is actually drooling, I sneered. Do you have any idea how pathetic that is? Decent women don’t react like that to being informed as to how repugnant they are, so I have to wonder – what the fuck is wrong with you? Are you just so stupid that you don’t understand the things I’ve written on your skin, or is it that you’re so thrilled that you’ve found someone who would consider fucking a fat cow like you that you’re willing to ignore it?

I’m sorry, Alexa again offered timidly.

I didn’t ask you to apologize, you ignorant whore, I growled, grabbing her hair tightly and pulling her face close to mine. I asked you why your disgusting cow twat is leaking all over your thighs, and I expect an answer. What is it, bitch? Are you so fucking pathetic that you still want to fuck me, even knowing that I find your body utterly repulsive in every possible way?

I guess, she quietly sobbed. I was glad that I made her strip first – if it weren’t for her visible wetness I would have honestly believed that she hated every aspect of what I was doing.

That’s unfortunate, I sighed. I’m afraid I have some bad news for you, bitch. I knew you were an ugly whore from your pictures, but I really had no idea just how much of a boner killer you were in real life. I know I said I might take your virginity, but I have my standards. Still, I did waste the day driving down here, and I suppose I can take a little pity on you and let you suck my dick – provided you get down on your knees and beg for it, of course. Maybe if you do a good enough job I might just bend you over and fuck that fat, flabby ass of yours.

Alexa looked surprisingly concerned; she was clearly more frightened by my threat of not fucking her than I expected. I was bluffing, of course – my cock was already growing hard just from humiliating her and there really wasn’t any way that I was going to pass up a chance to fuck her. Still, she seemed to have bought my act. She quickly dropped to her knees, tears still streaming down her face, and reached forward to unzip my jeans.

Unfortunately, she had neglected to beg me first. I considered letting it slide – god knows I had put her through enough already – but I didn’t want to set a bad precedent. I gave her another playful slap across the face and then forcefully shoved her back, causing her to land painfully on her ass. Alexa looked up at me, her face displaying confusion and fear.

I told you to beg, slut, I explained as she crawled back up to her knees. You didn’t actually think I’d let an ugly skank like you suck my cock just because she wanted to, did you? Come on, now – even you can’t be that stupid.

I’m sorry, she offered meekly. May I please suck your cock? I know that I don’t deserve to, but I promise I’ll do my best? I won’t tell anyone, so no one will ever find out.

I guess it would be cruel not to let you, I sighed. I’ll let you suck my dick, but don’t get your hopes up – I doubt I’ll be able to cum with a fat cow like you.

Alexa quickly crawled forward and unzipped my pants before I could change my mind. By that point I was rock hard, which probably undermined my bullshit story about finding her repulsive. Fortunately, I think she was far too afraid of pissing me off to actually say anything about it.

Wrapping her hand around the base, Alexa looked at it with confusion and fear. It was understandable – she was a virgin after all, and mine was probably the first cock that she had ever actually touched. Still, it felt inappropriate for me to just let her hesitation slide. Running my hand through her hair, I gripped it tightly and slapped her again across her face.

Alexa opened her mouth in surprise and confusion, giving me the opportunity I wanted. Still gripping her hair, I pulled her in hard and forced my cock into her mouth. After giving her a second to adjust, I began to fuck her face. Since it was her first time having a dick in her mouth I was careful not to penetrate her throat, but I still managed to be extremely rough with her. With each stroke she let out a pathetic, whimpering gargle, but I showed her no mercy.

What exactly is the point of my letting you suck my dick if you’re just going to go all passive on me? I asked her. All I’m really doing is jerking off with your mouth right now. If I wanted to do all of the work, I’d just use my hand – it’s warmer, tighter, and doesn’t make those disgusting whimpers you keep making. What a useless fucking slut you turned out to be; can’t even manage to suck a dick without embarrassing yourself.

Having told her what I expected I stopped guiding her motions with my hand. I maintained my grip on her hair just the same, but I let her take over how she moved her head. Unsurprisingly, she slowed down a little, though she continued going faster than I’m sure was comfortable. I considered correcting her lack of speed, but I decided to let it slide. I doubted she could maintain the violent nature with which I had been fucking her mouth earlier, and I didn’t want her to start thinking that I was some kind of a monster. Relaxing my grip, I let her do her thing for a few minutes in order to give her some time to adjust.

Getting bored already, I sighed. You’re not going nearly deep enough – you’ve really only sucked the first half of my dick. Is this your way of insulting me, by telling me that you find my cock so repulsive that you’d never actually suck the entire thing?

No! she exclaimed after wrenching her head off of it. That’s not it at all! It just won’t fit – if I go any deeper, I’ll throw up.

What the fuck do I care? I sneered, forcing my cock back into her mouth. If you can’t learn to suppress your gag reflex then maybe you deserve to suffer a little. Besides, it’s not like puking is going to make you any uglier. You have one minute, bitch – if you haven’t stuffed my entire cock down your throat and touched your nose to my belly button by then, I’m going to cum on your face and be on my way. I don’t really give a fuck, but if you don’t want to spend the rest of your meaningless life as two-thirds a virgin you should probably get your shit together and stop embarrassing yourself with such a pathetic excuse for a blowjob.

She looked up at me with her eyes and pleaded for mercy, but I ignored it. I knew that taking my entire length down her throat would be difficult, but I believed that she was capable. Either way, my threat to finish on her face and leave her was pure bullshit. I wasn’t about to be satisfied with having just fucked her mouth; even if she didn’t manage to deep throat me in the allotted time I would have just made up some lame excuse to give her another chance.

She didn’t try to do it all at once, which was probably wise. Instead, she went slightly deeper with each thrust. She was obviously struggling with the pain that my cock was inflicting on her throat; I could see the anguish in her eyes. I felt a little bad for her, but I couldn’t back out at that point. Relaxing my grip, I watched as she went deeper and deeper, until she had actually managed to stuff my entire cock into her mouth. She looked like she was about to vomit, but she also looked strangely proud of herself.

I was actually pretty impressed with her. I didn’t think that she would be able to take my cock down her throat so quickly and I felt like she deserved a reward. Grabbing her hair, I pulled her off of my dick and shoved her towards the bed. She looked slightly worried that she had offended me, though simultaneously grateful that the abuse to her mouth was over for the moment.

That was just sad, I sighed. In a screwed-up way, you’re actually lucky that you’re so fucking terrible at sucking dick – I don’t think you could make me cum with that talentless mouth regardless of how much time I give you. I’m a charitable guy, though, and I realize that it’s not entirely your fault that you’re so inexperienced. I’m going to let it slide – for now, at least.

Are you going to fuck me? she asked, sounding anxious, afraid, and hopeful at the same time.

God, no, I laughed. I wouldn’t fuck a fat cow like you even if you had done well, let alone after that abortion of a blowjob. I’m a charitable guy, but I’m not a fucking saint. What I will do, though, is fuck you up your asshole. It might not be exactly the same, but it’s about the best that a disgusting whore like you can hope for. Get yourself ready, bitch – I don’t plan to be gentle.

I reached into my jacket pocket and pulled out a tube a personal lubrication that I had brought specifically for that purpose and tossed it towards Alexa. She picked it up and shot me a confused look, probably wondering why I was demanding that she prepare herself for anal sex instead of doing it myself. I thought about doing it – god knows I wouldn’t have minded fingering her asshole – but it felt like it would be more humiliating to force her to do it while I watched. Tapping my foot impatiently, I tried to impress upon her that she was wasting time.

Alexa nervously squirted some lube onto her fingers, then reached down between her legs and began to slowly work it in. She looked absolutely mortified; I’m sure she would have liked some privacy. Unfortunately for her, her shame was a major turn-on for me. Besides, privacy felt inappropriate – I was about to ram my cock up her ass, getting shy that I was watching her just seemed silly.

God you’re slow, I criticized. You’ll regret that, you know. I’m going to be fucking your ass in a few minutes regardless of how ready you are. If you haven’t prepared yourself by then, it’s going to hurt like hell – but I’ll still fuck you hard and won’t stop until I’m done, regardless of how painful it might be. Get up on the bed, on your hands and knees, and start to really finger fuck your asshole. Don’t worry about looking like a slut or anything – I promise you, my opinion of you couldn’t possibly get any lower than it already is.

Alexa let out a humiliated groan but complied with my instructions just the same. Climbing up on the bed, she got down on all fours and reached back to continue finger-fucking her own asshole. She was slightly more aggressive than she had been before, though I suspected that it was because she was no longer facing me and therefor was able to pretend that she was alone. I appreciated the added aggression, but I didn’t want her to forget about me and get too comfortable.

Faster, bitch, I instructed. You’re supposed to be stretching your asshole out and getting it nice and slippery, not just fucking yourself in the wrong hole. God, you’re really enjoying fingering your own asshole, aren’t you?

A little? she replied nervously. Her voice reeked of shame, but I also heard a good amount of lust in it as well – I suspected that there was nothing little about her enjoyment.

That’s just pathetic, I laughed. You really are a dumb whore, aren’t you? You’re not supposed to enjoy it in the ass, slut. Hell, that’s a big part of why I’m using that hole – you simply don’t deserve the pleasure of getting fucked like a real woman. Maybe you’re just too stupid to understand the difference between your cunt and your asshole, but I’m willing to help fix that. You’re stretching your ass out with your right hand like a good little bitch, but you’re not doing anything with your left hand. Use it to play with your clit, slut – god knows no one else is going to do it for you.

Alexa obeyed my order much quicker than I expected. Burying her face in the bed, she reached back with her free hand and began to fuck herself aggressively. I suspect that she was extremely turned on and desperately wanted to play with herself, but was too embarrassed to do so without explicitly being told by me.

As I watched her degrade herself I quickly stripped out of my remaining clothing. I was enjoying the show, but I was also feeling impatient. My cock was throbbing, and I wanted to do something with it quickly. Alexa had managed to fit two fingers up her ass by that point, but I suspected that she could be doing more.

Getting real bored here, bitch, I sighed. It’s bad enough that I’m going to disgrace myself by fucking a fat pig like you in the ass, but making me wait for it is just completely unacceptable. I’m not sure if you’re incompetent or just trying to insult me, but I can promise you that you’ll regret it soon either way.

I’m going as fast as I can! she protested. Please don’t be angry, I swear to god that I’m not trying to insult you!

You say you’re going as fast as you can, but I’m pretty sure that you could go faster, I shrugged. How about this – you have one minute to get yourself ready. After that, I’m going to shove my dick right up that fat cow ass of yours whether you’re ready or not. If you’re ready, fine. If not, try to keep the whimpering down – fucking your ass is disgusting enough without having to listen to you crying.

Alexa groaned loudly, but forced a third finger up her ass. As she began to pump them in and out it was apparent that it was painful to her, but I figured she could take it. Sure, it might hurt her, but it would be less painful in the long run than getting fucked in her asshole unprepared. Besides, watching her hurt herself like that was a major turn-on – I was already regretting promising her a full minute.

It took her about thirty seconds before she had adjusted to the third finger. Not wasting time, Alexa forced a fourth finger up her ass and began to very slowly pump them all in and out. She wasn’t able to go very deep, but it was still fun to watch. A part of me considered giving her more time just to see how thoroughly she could degrade herself, but I chose not to – I really didn’t feel like waiting much longer.

By the time the minute ended she had managed to get four fingers into her ass almost all the way up to the final knuckle. I was impressed – she obviously was willing to really hurt herself for my amusement, and I liked that. Unfortunately for Alexa, I was also impatient. I’m sure she could have benefitted from more time, but I was done with waiting. Besides, I figured she was prepared enough that she wouldn’t be in any overt medical danger – it just might hurt a little more than she’d prefer. Approaching the bed, I grabbed the tube of lube and rubbed a some onto my throbbing cock.

That’s enough time, slut, I informed her. Hopefully you’re ready; if not then let this be a lesson to you. An ugly cow like you should always be prepared for an ass-fucking. Sure, your repulsive layers of fat will keep most men away from you, but on the off chance that someone is feeling charitable you ought to be prepared – and someone as hideous as you certainly isn’t going to be taking it up the cunt. Get your fingers out of your ass and brace yourself – I’m not planning to go in gentle.

Alexa nervously removed her hand from her asshole. Surprisingly, she continued to finger fuck her pussy as I got into position, even though I hadn’t explicitly ordered her to do so. I couldn’t blame her – I could both see and hear how tremendously wet she was, and I suspected it might even be painful for her to stop. I thought about ordering her to stop just because of that, but decided to be merciful – I was about to put her in enough pain as it was without adding sexual frustration.

Placing one hand on her hip, I used the other hand to guide my cock into her asshole. Even with the preparation she had done she was still extremely tight – I had to press hard just to get the tip in. I considered ramming it into her painfully, but decided not to. Although I had threatened that I would, I didn’t want to actually hurt her so bad that it would be medically necessary for me to stop. Fighting against my growing desire, I forced myself to go extremely slowly.

Apparently it was a good thing that I did go slowly. As I gradually forced inch after inch of my cock into Alexa’s virgin asshole she whimpered loudly in pain – I’m sure if I had started quickly she really wouldn’t have been able to take it. She was obviously hurting, though that pain didn’t seem to be doing much to turn her off – even with her pathetic cries I could still here the wet sloshing noises of her fingers rapidly pumping in and out of her twat. Reminding myself of how much it had hurt when she was ignoring me, I continued to force myself into her as she grunted in extreme pain.

It took a while, but eventually I was buried up to my balls in her ass. Alexa was crying pretty heavily, but she still continued to fuck herself with her left hand. Keeping my cock buried in her, I reaching forward, grabbed her by her hair, and pulled her face up. I wanted to see her anguish and I didn’t like her hiding her face in the bed. I knew that I should have felt bad for hurting her, but I was drunk with power and a feeling of retribution for how she had hurt me in the past.

Congratulations, bitch, I laughed. You’re finally getting ass-fucked. Most women would be horrified to be getting fucked up the ass by a man who clearly doesn’t respect them, but you know better than to think that, don’t you? Tell me that you know this is all you’re worth and you should be grateful for it, bitch.

This is all I’m worth, she groaned, her voice soaked in lust and shame. ‘I’m grateful for it – I know that you’re doing me a favor by fucking me in my fat ass.

I gave her a few more moments to adjust to having my dick up her ass, and then began to fuck her slowly. It was actually fairly difficult for me – every part of my instinct screamed that I should just pound her as hard as I could – but I managed to force myself to move at a snail’s pace. I’d like to say that Alexa appreciated my restraint, but really she just continued to whimper in pain.

It wasn’t just pained whimpering that I heard, though. Listening carefully, I could make out rhythmic moaning hidden inside her cries. It actually sounded kind of like she was consciously trying to disguise the fact that she was enjoying what I was doing to her. I didn’t really mind, but I liked the idea of further humiliating her. If she was ashamed of the fact that she was getting off on being abused, I wanted to bring that out into the open.

I can hear you moaning, you fucking slut, I informed her. I don’t know why you’re trying to hide it, either – I could have guessed how much a disgusting whore like you would love getting her dirty little asshole fucked.

I’m not trying to hide it! she protested. It just hurts!

Well, then you should have done a better job getting ready, I shrugged. I mean honestly – you didn’t think I was going to fuck you in that flabby excuse for a cunt that you have between your legs, now did you? You should have known that you’d be getting fucked in your ass, and you have no one but yourself to blame for that. Moving forward, I want to hear you moan like the slut you are. If you want to ever have a chance of getting fucked in the pussy, you had better make me believe that you’re having the time of your worthless life right now.

You’ll actually fuck my pussy? she asked.

I’m not promising anything, I laughed back. However, if you lose ten pounds or so and we put a bag over your head, it might not be completely out of the question. You’re getting ahead of yourself, though – right now, you should be focused on letting me know how much you love getting your disgusting pig asshole fucked before I lose interest in you entirely. Let me hear you moan, bitch.

Alexa began moaning openly. The timing would have made me suspect that she was just faking it in order to obey me, but the moans sounded legitimate – if she was faking it, she was significantly better at faking it than any virgin should have been. I suspected that it was just like when I had ordered her to fuck herself – she secretly wanted to do so all along, but was too ashamed to actually do it until after I had explicitly ordered her.

I continued to fuck her at an extremely slow pace for a minute or so, listening as the pain in her moans gradually faded away. Figuring she could handle it, I began to slowly build up speed. I paced myself – I didn’t want to tear her apart or anything – but after a couple more minutes I was fucking her ass at a reasonable pace. Gripping her hips with my hands, I drove into her with long, solid strokes.

By that point it sounded as though Alexa had almost completely gotten over the pain. There was still a hint of discomfort in her moans, though I suspected that was just as much from the humiliation that I had inflicted as any physical damage. Even that was fading – it sounded as if she had almost forgotten the degrading things that I had said and done to her. I liked the fact that she was enjoying herself, but I didn’t want her getting too comfortable – I was enjoying her suffering far too much to just let it end.

You sound fucking ridiculous, slut, I criticized. I realize that I’m the one that told you to moan, but hearing a fat pig like you making human sounds is just unsettling. Let’s try something a little more natural – I want you to stop pretending that you’re a woman and act like the pig you are. Oink for me, bitch.

Alexa turned her head to look back at me and shot me a look of absolute horror. She begged me with her eyes to cut her some slack and rescind my order, but I wasn’t feeling merciful. Forcing her to literally squeal like a pig wouldn’t actually do anything for me, but I knew it would be extremely humiliating for her and that was what I cared about. Hoping to impress upon her that she should have obeyed me by then I drove my cock into her ass hard, causing her to cry out in pain.

Alexa’s face was bright red with shame, but she forced out a reluctant oink. I could tell how much it hurt her to have to do such a degrading thing, but I still wasn’t satisfied. Grabbing her by her hair, I jerked back hard while thrusting into her to let her know that I wanted more. As tears of shame ran down her face, Alexa forced herself to let out a stream of humiliating oinking sounds, timed to correspond with my sadistic thrusts into her ass. I could tell that she hated it, but I could also here the lust in her voice – whether she wanted to or not, she was getting off on being forced to imitate a pig. I didn’t want to get my hopes up, but it actually sounded like she was approaching orgasm as well.

You know, I stated, fucking you in your fat ass isn’t quite as bad as I thought it would be. Especially with looking away from me, I can just close my eyes and pretend that I’m with actually fucking a real woman instead of some disgusting whale. Plus, you’re easy – most women have too much dignity and self-respect to just bend over and take it up the ass, but you apparently realize that that’s exactly what you’re for. Don’t get the wrong idea or anything – I most certainly don’t love and respect you – but I might actually be willing to do this again in the future. You’ll never be my first choice, of course, but when I’m unable to get someone less disgusting I think I’ll throw you a bone. How’s that make you feel, bitch?

Will you fuck my pussy next time? she asked.

We’ve been through this, bitch, I sighed. If you want me to fuck your disgusting little pussy, you’re going to need to lose ten pounds and get a burlap sack for your head – preferably something extremely thick. As it stands, you’re far too disgusting to me to fuck in any hole other than your ass or mouth. It’s critical that you understand this concept – I don’t want you forgetting your place and assuming that you’re anything more than just a convenient place to dump cum. Explain to me why you don’t deserve to get your pussy fucked, bitch.

Because I’m fat? she offered lamely.

Not good enough, I growled, jerking hard on her hair for emphasis. I’m not looking for a few words; I want you to really explain it. Be elaborate, be vulgar, and spare yourself no dignity. If I have to warn you again, I promise you that you’ll regret it.

I don’t deserve to get my pussy fucked because I’m a stupid fat cow, she moaned. I’m far too disgusting for that honor, and you probably couldn’t even stay hard while fucking me anyway. The best I can hope for is getting my fat cow ass fucked, and I should be extremely grateful for that.

Good slut, I laughed. Moving forward, what do you need to do if you want me to fuck that disgusting slime hole that you call a pussy?

I need to lose ten pounds, she moaned, and get a thick bag to cover my head.

You’re paying attention, I acknowledged. I like that. Now, I’m sure you know why you need to lose weight – aside from the fact that you’re disgusting as you are, there’s logistical concerns. I’m not even sure I’d be able to reach your twat with all those rolls of fat surrounding it. I’m curious, though – why do you think you need to have a bag over your head?

Because of how ugly I am? she guessed. That way you don’t have to see my disgusting face when you fuck me, and you can pretend that I’m someone you’d actually fuck willingly.

You catch on quick for such a stupid bitch, I laughed. You’re right though – that’s exactly what the bag is for. In fact, I might force you to help me pretend that you’re someone else. You wouldn’t have a problem with it if I called you a different woman’s name, would you bitch?

Not at all, she moaned. If you were fucking me, you could call me anything you wanted. I’d just be happy for the attention, even if that attention was meant for someone who isn’t me. I know that I don’t deserve it anyway, so it’s only fair.

I’m glad you understand, I replied. I’m going to want you to help with that, too. We’ll meet again here next weekend, and I want you to bring some things. Obviously you’ll have to bring a bag for your head, but I want you to bring a few pictures of your female friends as well. Headshots, specifically. If you manage to earn the right to lose your virginity then I’ll pick one that I would actually fuck, and tape her picture onto your bag. It will be horribly degrading to you, of course – I’ll expect you to answer to her name and everything – but if you play your cards right, you might not end up dying a virgin after all. You don’t have any problem with this, do you bitch?

I don’t, she moaned in response. I understand that a fat, ugly cow like me can’t be too picky, and I’m grateful that you would even consider disgracing yourself by fucking me. I’ll do anything you tell me to in order to make it less disgusting, I promise.

It sounded like she was actually getting extremely close to orgasm. Unfortunately, having her verbally degrade herself was pushing me along pretty effectively as well. I tried to hold myself back, but the corrupt things that I was forcing her to say coupled with the insanely pleasurable feeling of fucking her ass was too much for me to withstand. I realized that I was going to cum and there was nothing that I could do to stop myself.

Gripping her hair tightly, I drove in hard until I was buried up to my balls in her ass. Grunting loudly, I pumped what felt like gallons of semen into her formerly virgin asshole as Alexa squirmed in pain. Her face contorted with pleasure, humiliation, and pain as I emptied my balls into her vulnerable asshole.

Exhausted, I collapsed on top of her, pinning her down under my weight. I considered pulling out of her, but decided not to – even though my orgasm had ended I could still feel cum trickling out of me and into her. I liked the idea of filling her up and having it slowly leaking out of her, reminding her of the things that I had done to her, and I wanted to make sure that all of my semen got inside her. I’m sure that it was a little uncomfortable for her – after being fucked in the ass for the first time she was likely sore and eager to get my dick out of her – but I figured she’d live. Besides, we still had time and I wasn’t quite done with her yet.

Continue reading with chapter two.

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