I knew what Madison wanted. She might have believed that she had already figured out the secrets of the universe and was far smarter than everyone, just as countless other high school seniors had before her, but in reality she was completely transparent. She was failing my class and she was hoping to bullshit her way out of the consequences so that she could graduate on time. I didn’t know exactly what specific flavor of bullshit she might try to feed me, but I wasn’t nearly as oblivious to what was going on as she might have hoped. It wasn’t my first rodeo.
Under different circumstances I probably would have cut things short, told her exactly what additional work she would need to do in order to earn a passing grade, and been done with it. I generally have no interest in torturing students, and with the school day being over I was eager to get home already. Madison was different, though. She was my daughter’s best friend and chief corrupter. I quite enjoyed seeing her squirm.
Madison and Leah had been close ever since they were both twelve years old. Even back then, Madison was a bad influence – she taught my daughter how to shoplift and expanded her vocabulary to include words that shouldn’t be said in polite company. As the girls aged things only got worse. When Leah was caught ditching school, I knew who she was ditching with. When I smelled tobacco smoke on Leah’s breath, I knew where she got it from. I had always been tempted to simply put my foot down and forbid Leah from associating with Madison, but it felt like doing so would be unfair to Leah. Leah didn’t have a ton of friends, and as much as I hated Madison’s negative influence on her I didn’t want to isolate her socially.
So, Mister Rivera, she finally began.
I’ve noticed you looking at my body, and I’m hoping that we might be able to work out something with my grade.
I suddenly wasn’t quite so happy about the situation. Madison might have had a reputation as a problem child, but if she were to tell the wrong people that my eyes occasionally drifted in an inappropriate direction she could easily drag my reputation down with her. Teaching twelfth grade history is a strange thing – the students are legally and biologically adults, yet we’re expected to pretend that we never view them that way. Everyone knows it’s bullshit, of course – any healthy adult man is going to be attracted to a smoking hot eighteen year old girl like Madison whether he wants to be or not – but that only seems to make things worse. If I deny that I’ve had sexual thoughts I look like a liar, if I admit it then I’m a pedophile. Once the accusation is made, there’s really no winning strategy.
Where exactly are you going with this? I shot back, trying to sound confident yet bored in the hopes of making her think that I wasn’t the slightest bit worried.
I’d like to get home already, Madison, so if you could just spit it out already I’d really appreciate it.
Fine, she shrugged.
You give me an A, and I’ll give you a blowjob. Your wife’s been dead for three years now, and Leah tells me that you haven’t had a girlfriend since. Change one little letter which doesn’t cost you anything, and instead of jerking off in your bedroom once you think Leah’s asleep I’ll suck your dick.
I would normally be pretty angry about the crass way that she had spoken about my wife’s passing, but mostly I was just relieved. Madison wasn’t trying to blackmail me; she was trying to bribe me. The balance of power was once again in my favor.
You’re kidding, right? I smirked.
I give you an A, and then what’s your report card look like – F, F, F, A, F? Yeah, that won’t raise any suspicions. Here’s the thing, kid. You never do homework, you never study and it shows – even a D would look questionable on your report card. As fun as it would be to see your embarrassing teenaged understanding of how you think oral sex works in action, I think I’m going to have to pass. Somehow I just don’t think you’re that good. Now if you’ll excuse me, I have to be getting home.
You’re wrong, she shot back as I rose to my feet.
I may be young, but I know how to suck dick. In fact, I might just teach Leah my secrets this summer; assuming I don’t get to go to Europe on account of the fact that I’m stuck in summer school.
Her thinly-veiled threat struck a nerve. Madison knew how much I despised her negative influence on my daughter, and threatening to turn Leah into a slut like her was absolutely not okay. I shot her an angry glare, hoping that she’d understand that she was well over the line and back down. Rather than realizing how unacceptable her threat was, though, Madison responded with a smug grin; as if to let me know that she believed she had some power over me. It felt almost as if she were silently challenging me; mocking me for my inability to stop her. Losing my temper, I stepped forward and slapped her across the face. I managed to hold myself back a little, but I hit her hard enough to knock her down to the floor.
You fucking psycho, she hissed, bracing her face with her hand.
You can forget about the blowjob, by the way. You’re giving me an A now, or I’m going to the cops.
Go right ahead, I bluffed.
You think anyone’s going to believe a stupid bitch like you?
Here’s what really happened, officer – she told me that if I didn’t give her an A then she’d hit herself and pretend that I did it. I’m a respected member of this community, Madison. You’re a piece of garbage that will no doubt spend the majority of her adult life in and out of correctional facilities. You don’t think anyone is actually going to take your word over mine, do you?
I watched with delight as Madison’s facial expression contorted from one of smug security into impotent rage. I knew I should have felt bad about what I was doing – I was blatantly exploiting my position of power in a way that was completely unfair and ethically disgusting – but at that moment I really didn’t care. I was still angry about her threat to
teach Leah how to perform oral sex, her disrespectful comment about my wife, and her historical corruption of my daughter. Mimicking her actions from earlier, I shot her a smug smile as if to dare her to do something about it.
Madison didn’t seem to appreciate my actions any more than I had appreciated hers. Springing to her feet, she lunged and me and punched me in the gut as hard as she could. I was actually impressed – even though she was half my size, she managed to hit pretty damned hard. Enraged, she then did her best to claw my eyes out.
Unfortunately for Madison, though she might have had some impressive tenacity on her side her plan was hardly without flaw. Once I got over the initial surprise of her punch I was able to easily grab her wrists and restrain her. To her credit, she didn’t give up – she continued to struggle even after it was clear that she really didn’t have a chance. As she flailed about futilely, I forced her over my desk and pinned her arms behind her back. Even bent over and in such a vulnerable position, she still tried to fight me.
Let it all out now, little girl, I laughed, intentionally sounding as patronizing as possible.
Go ahead and struggle to your heart’s content – I’ll let you go as soon as you’re all tuckered out.
You think this is over? she growled.
I’m not going to let you get away with this, motherfucker. It might not be today, but I promise you I’ll get you back for this.
I’m sure you’ll try, I replied.
And when you do, I’ll just overpower you and restrain you again. Maybe next time I’ll turn you into the police for assaulting me, maybe I won’t. I guess we’ll just have to wait and see.
I never said I’d attack you like this again, she hissed.
You’re right, and I can admit that – you probably would just overpower me again. I don’t think Leah’s quite as strong as you, though.
Are you actually threatening to beat my daughter to get me back? I asked, appalled that even Madison could suggest such a thing.
She’s your friend, you fucking psychopath.
She is, Madison agreed,
and no, I won’t be attacking her physically. I would never want to hurt her; I only want to help her become a woman. Don’t get mad, now – I know you don’t want me teaching her how to suck dick – but there’s other things I can teach her. She’s still a virgin in the other two holes, but she won’t be for long. Make sure that you keep her on the pill, by the way – guys hate it when you ask them to use condoms. And hey, since her mouth won’t be occupied with strange cocks, maybe I’ll teach her how to eat pussy instead – I’m betting sweet little Leah has a very talented tongue on her.
I knew what she was doing. She was trying to make me lose my temper by saying disgusting things about my little girl; probably in the hopes that I’d get so enraged that I’d make a mistake and give her an opportunity to turn the tables on me. The correct strategy would have been to keep my calm and laugh at her impotent threat, but I didn’t care. She had no right to even say such filthy things about Leah, and I wasn’t about to let that stand. Rage taking over my actions, I flipped her slutty short skirt up and slapped her across her ass as hard as I could, leaving a bright pink handprint where I had struck her. Madison let out a pained yelp, but quickly regained her composure.
That was kind of hot, she moaned.
I wonder if Leah is into the rough stuff too. I’m sure we’ll find out – you know how guys are. I doubt I’ll even have to suggest it; some loser will probably bend her over and spank the little bitch’s ass while he plows her from behind just because he feels like it. She does have an utterly spankable little ass, after all – but I’m sure I’m not telling you anything you didn’t already know.
Watch yourself, I growled.
You’re playing with fire here, bitch, and you really don’t want to continue. Keep threatening my daughter and I promise you I will make you regret it.
You misunderstand! she protested, feigning innocence.
I’m not threatening her at all. I would never have Leah spanked to hurt her, I just think she might enjoy it. Lots of girls do, you know – I mean, I’m not going to lie to you here, my pussy is already juicing up from when you hit me. Go ahead and check, I don’t mind.
I don’t know what I was thinking, but I took her up on her offer. I just wasn’t thinking straight – I was so blinded with anger at her for talking about Leah the way that she was and fear that she might actually make good on her threats. I’m sure on some deeper level there was just the standard instinctual desire for pussy, as well – Madison might have been a waste of genetic material, but I couldn’t pretend that she wasn’t also a smoking hot piece of ass. While I may not know exactly what my motivation was, I know what my actions were. Keeping her pinned down with my right hand I brought my left to her crotch. Taunting me, she parted her thighs slightly; as if to dare me to continue. With no interest in backing down, I slipped my fingers around the crotch of her panties and into her slit. Just as she had claimed, she was getting wet.
See? she moaned.
Just like I said, lots of girls like being spanked. I wasn’t threatening to hurt her; I was just saying that giving the little slut a nice spanking might make things easier on her. A lot of the guys I know have some pretty big dicks, so we’re going to want her pretty little virgin pussy soaking wet before they ram them up her. We wouldn’t want her to have a bad experience and dislike sex, after all – especially with all the cocks she’s going to be taking.
I’m not going to warn you again, I threatened, slipping back into rage mode.
You do not speak about my daughter like that. You do not think about my daughter like that. I swear to god, bitch, I am not going to let you turn her into a filthy whore like you.
I know why that is, she laughed.
It’s because you want to do it yourself, isn’t it? You’re not angry that someone’s going to fuck Leah up her tight little asshole, you’re angry that that someone doesn’t happen to be you. You should really get over it, Mister Rivera. From what I hear, you can’t even get it up – if Leah has to wait for your pathetic little limp dick she’ll probably end up dying a virgin. That wouldn’t be very fair to her, now would it?
I knew that she was manipulating me, but she was doing a damned good job at it. Again losing my temper, I pulled my hand out of her panties and spanked her ass hard. Madison yelped in pain again, though her voice had a much more lustful tone than it had the last time. I immediately regretted losing control of myself, but it was too late to take it back.
I know what that means, she taunted.
You know how much I enjoy a nice hard spanking, so you’re trying to tell me that I’m right and rewarding me for my cleverness. I don’t want to be ungrateful or anything, but it’s unnecessary – really, it doesn’t take much insight to know that you’re an impotent little pervert. I mean, just look at the situation we’re in now – you have me bent over your desk with my skirt hiked up and my innocent little teen pussy dripping wet. You could prove me wrong easily by pulling my panties down and showing me just how hard you can get, but you won’t. You’ll just give me another boring-ass lecture, because you know your faggot ass could never actually fuck such high-quality pussy as mine. Do me a favor and just wake me up when you’re done droning on, if it’s not too much trouble.
The irony of the situation was that for all of her claims that I couldn’t get it up, my cock was straining against the inside of my pants to break free. I don’t know if it was the physical combat with her, the feel of her pussy, or even just the fact that it had been so painfully long since I had last been with a woman, but I desperately wanted to prove to her just how wrong she was. I knew it was a mistake, and I knew that I was only playing into her hand, but I really didn’t care. Reaching down with my free hand, I undid my pants and let them fall to my ankles. Grabbing her panties, I pulled them down as well.
Is that supposed to intimidate me? she laughed.
Please, old man – I know you’re bluffing. Sure, maybe you can get it hard, but what difference does it make? You don’t have the balls to do anything with it, anyway. At least, I assume you’re hard – usually they’re a bit bigger than that tiny little thing. Does it really not get any bigger than that? I’m beginning to understand why you’re such an asshole – going through life with a second belly button must have been very stressful for you.
I’m not an idiot. Her manipulation couldn’t have been any more obvious to me, but that didn’t really matter anymore. It might have been precisely what she wanted me to do, but it also felt like the right thing. I had to choose between stuffing my cock back into my pants and walking home in frustrated shame, or fucking a smoking hot piece of ass and proving to her that I was not only capable of doing something with my dick, I was big enough to make sure she felt it.
Keeping my grip on her wrists, I positioned my body directly behind hers and aimed my dick with my free hand. By that point Madison was dripping wet; the head slipped in without any difficulty. She let out a dismissive sneer, as if to suggest that she still thought I was bluffing and I’d back off any second, but I didn’t care. If I’m honest, at that moment I cared a lot more about getting some pussy than proving myself. Still, I wanted to make sure she understood just how wrong she had been. Bracing my free hand on her hip, I thrust into her fully as hard as I possibly could. Madison grunted in surprise and pain – I don’t think she expected me to be so rough with her, but she probably should have.
Not so hard, she grunted.
You’re hurting me!
I don’t see how that’s possible, I laughed, fucking her at a brutal pace.
I mean, a slut like you who has no doubt had countless anonymous dicks inside of her must be all stretched out, and as you’ve so eloquently pointed out I’m equipped with little more than a
second belly button – frankly I’m amazed you feel this at all. Surely you can handle a man as tiny as me, right bitch? This shouldn’t even faze you.
It doesn’t, she lied, obviously in a lot more pain than she would have liked me to know.
I’m just trying to spare you some embarrassment. It sounds like you’re trying so hard to make me feel this, and I wouldn’t want to hurt your feelings when I barely even notice that it’s over.
Good point, I replied, playing along with her bullshit.
Though, maybe I’m just in the wrong hole. Maybe I’d be more effective if I chose to fuck you up the ass instead. I don’t have anything to lube you up with, of course, but with something as tiny as me I doubt we really need lubrication. Should be able to just shove it straight in there as hard as I can; you probably won’t even notice.
I watched as the confidence drained out of Madison’s facial expression. She must have known that I knew how full of shit she was – the stressed grunts that she tried and failed to restrain with each thrust made her story that she could barely feel me difficult to believe. I’m sure that she realized how painful and probably medically dangerous it would be if I were to fuck her ass as hard as I was fucking her pussy, but she seemed to think that I might just be bluffing. Hoping to demonstrate how serious I was, I pressed my forefinger up against her asshole and roughly forced it in, causing her to whimper in pain.
So what do you think, bitch, I taunted.
A little slut like you can’t possibly be satisfied with such a tiny thing in her sloppy little pussy; it seems like not fucking you up your whore ass would almost be cruel. In fact, I shouldn’t even be wasting time asking – I’ll just spare you the trouble of having to state the obvious and shove it in there.
Wait! she cried out.
Look, I was just kidding – you’re big enough for me to feel. Please don’t fuck me in the ass; I think you might kill me if you do.
Not nearly good enough, bitch, I growled, thrusting my hips forward hard.
I don’t give a flying fuck about how big or small you want to pretend my dick is, but I do want to see you suffer. I warned you about talking about Leah and you decided to continue anyway. If verbal instruction isn’t enough to get through your thick skull, then maybe getting your whore asshole torn open will get the message across.
I’m sorry, she whimpered.
I didn’t mean the things that I was saying; I was just trying to make you mad. I honestly never would do any of those things to Leah; I was just desperate to get my grade changed. Please don’t fuck my asshole?
I probably should have stopped there. Madison was clearly afraid, and I was sure that I had gotten my message across. Unfortunately for her, I was deeply enjoying the terror she was experiencing. She had always been so tremendously disrespectful towards me; having her actually fear me was completely new and highly enjoyable. I knew that I should have stopped myself and settled for what I had already accomplished, but I just couldn’t bring myself to let things go back to the way that they were. I had her paying attention to me for the first time in her life, and I wasn’t about to give that up so quickly.
I just don’t know, I sighed, continuing to fuck her pussy hard while keeping my finger up my ass.
I’m real sorry, Madison, but I just don’t think I can trust you. It’s nothing personal, you know, it’s just that you’re kind of a lying little slut whom only an idiot would trust. I’d really like to believe that you’ll keep your word about not corrupting my daughter just because it’s the right thing to do, but I just don’t think I can.
I swear to god I will! she pleaded.
Just please don’t fuck my asshole and I promise you I’ll never be a bad influence on Leah again!
You’ll never see Leah again, I corrected her.
At least outside of school. You won’t talk to her, text her, and you damned sure won’t hang out with her. Is that clear, bitch?
Madison shot me a pleading look. Under different circumstances I might have been sympathetic to her position – she had been such close friends with my daughter for so long that it was probably a bit cruel for me to demand that she immediately end things. At the moment, though, I really didn’t care. I still had her threats about corrupting my daughter sexually on my mind, and I wasn’t inclined to show any mercy. Glaring at her, I forced a second finger up her ass just to let her know that I wasn’t open to negotiation.
Okay, she whimpered.
I won’t talk to Leah anymore. Now will you please take your fingers out of my ass?
You’re goddamned right you won’t, whore, I growled.
And I swear to god if I catch you talking to her, I’m going to do so much worse to you than just fuck you in your ass. Trust me, bitch – I know that a slut like you might not mind a little anal, but I promise you that I can come up with something that you won’t enjoy in the slightest.
Having made my point I pulled my fingers out of her asshole and slapped her hard across her ass again. I knew she’d probably enjoy it on some level, but I didn’t really care – the truth was that I deeply enjoyed hitting her and wasn’t all too concerned as to how she would take it. As she moaned in response to the spanking, I figured that I no longer really needed to restrain her. Releasing her wrists, I slid my hands under her body and up her shirt. I knew I probably would never get another chance to really take advantage of a student like that, and I wanted to make it count. As I continued to plow into her from behind, I explored her body with my hands.
With the threat of rough anal sex off the table, Madison’s mood changed quickly. There was still a look of minor fear in her face – I’m sure she realized that I could easily change my mind about raping her in the ass if I chose to – but overall, she seemed to be enjoying what I was doing to her. She moaned loudly as I fucked into her, and even began to fuck me back.
The emotional experience was overwhelming. I was simultaneously ecstatic that I was finally getting a little revenge on Madison and disgusted with myself for what I was doing. I hated and pitied Madison, and I hated myself even more. With my mind drenched in chaos, my instinct took over. I forgot all about the moral issues of what I was doing and focused exclusively on what my animal side desired. I fucked her brutally – I wasn’t so much making love to her as attempting to stab her to death with my cock. She seemed to react well to that, though. After ten minutes of my brutal assault, Madison came loudly.
Watching Madison’s orgasm was a unique experience. It helped me to feel a lot less guilty over what I had done, but it also made me feel powerful. As her body convulsed in orgasmic pleasure I felt like I had truly conquered her; for the first time even it seemed like she accepted that she had been beaten. The feeling of victory was immense, and easily enough to push me over the edge myself.
I thought about cumming inside of her, but I decided not to. I wasn’t sure if she was on the pill or not, and I realized that I’d probably have enough shit to deal with after what I had done without knocking her up. Additionally, I wasn’t convinced that she wouldn’t head down to the police station and tell them that I had raped her; and I didn’t want to leave her dripping with genetic evidence. Pulling out, I grabbed her by her hair and pulled her off of the desk and onto the floor.
Sensing what was going on, Madison opened her mouth willingly. Maintaining my grip on my hair, I forced my dick into her mouth as I felt my orgasm beginning. Wanting to see just how skilled she was orally, I forced it down her throat as semen spewed out. Surprisingly, she managed to take my entire length without gagging. A part of me regretting questioning her blowjob skills earlier, but I didn’t really care. Grunting loudly, I shot my load directly down her throat as she struggled to swallow it all.
After emptying my balls into Madison’s stomach, I pulled my cock out of her mouth and pulled my pants back up. My mind was racing – without the high of sex to distract me I was beginning to realize that I had just done a very, very bad thing. As Madison rose to her feet and straightened her clothes I realized that I was probably going to have to give her something if I didn’t want to lose my job or worse.
I’ll give you a D, I stated.
It’s passing, and it won’t raise suspicion the same way it would if I gave you an A. I’m going to need you to work with me here as well – start actually doing homework, paying attention in class, et cetera. I need it to look like you might have possibly earned it – If the administrators find out that I’m changing your grade because I fucked you then it’ll certainly fuck up my life, but it won’t do you any favors either. You’ll just get another teacher, and he’ll most likely give you the grade you deserve. Understood?
Understood, she grinned.
I’ll meet you halfway, but if you even think of failing me I promise you I’ll make you regret it.
Having said her piece, Madison walked out of the room. Aside from the fact that she was walking slightly funny, she showed no signs of what had just happened in the classroom. I wasn’t sure if that was a good thing or not – I was glad that she wasn’t so traumatized that she’d raise suspicion, but I knew how manipulative she could be. I worried that she wouldn’t settle for a single letter grade improvement, and I didn’t trust her to set her sights on something believable.
Feeling as if I was in a dream, I grabbed my things and drove home. I knew that I’d likely have to deal with some serious fallout from what I had done, but I wasn’t sure what I could do about it at the moment. I didn’t like it, but the truth was that I would just have to wait and see what happened next.