Around that time, however, I’d discovered certain methods for payback that nobody was probably expecting. Blackmail being my favorite out of them. It started out with me eavesdropping on private conversations between classmates, things often involving drugs or liquor, and me threatening to rat them out if they didn’t give me what I wanted. I usually ended up taking their money or just smacking them around for a little while. It made me feel powerful, and that wasn’t a feeling I planned on losing anytime soon. Then I took things further and started blackmailing girls that rudely rejected my advances. The first one was a bitchy cheerleader I’d filmed smoking a joint in the woods near her house while I was walking home. Her father was known to be strictly against that type of thing and was rumored to even be physically violent to get that point across to his children. I guess those rumors were true, because it didn’t take long for her to sink to her knees and beg for my silence on the matter. Still got some pretty fun memories of her on her knees with my dick slapping against her pretty little face. Sadly, she moved to another state only days later. After that, I’d done the same to a handful of other girls. Months later, me and my family moved to another town in central Indiana and I was enrolled into the local highschool. Didn’t take long to find another potential target.
Most of my teachers here treat me well, and I get along with them better than most of my classmates. I have some friends within the student body here and there, just not quite as many. There’s one exception to this though, because my sixth period history teacher doesn’t treat anybody well, especially not people like me. She belittles every student that doesn’t agree with her teachings, even though many of them are historically proven to be wrong. She even took to picking on my sister regularly because she can’t talk as well as she “should”. My sister, Millie, is four years younger than me and has Asperger’s Syndrome. She’s gifted in ways of academic intelligence, but she’s impaired when it comes to coordination and socializing. She stutters relatively often and the teacher, Miss Wells, has no patience for that. I’m not gonna pretend I’m some sort of saint, I know I’m an asshole for what I’ve done to people, but I’ve always looked out for my sister. Don’t plan on stopping anytime soon either. Obviously, it was her attitude towards Millie that initially drew me to the thought of screwing with her life somehow…but the plan was quite different at the start then it currently is. I was originally planning on just humiliating her in front of the class under the threat of leaking compromising some secret I had yet to find.
Then I started noticing her body. She was an older woman, mid or late thirties, but she look considerably younger and was quite fit. She jogged fairly often around the neighborhood, and she sometimes past by my house. I’d caught glimpses of her through the window at times. Her legs had just enough muscle and her tits, while not the biggest I’d seen, were perky and seemed pretty firm. Her jogging shorts hugged her ass well enough for me to think it was much the same way. Her figure was actually kinda similar to one of my favorite films stars, Jessica Alba. That, combined with her shoulder-length dirty blonde hair and dark blue eyes, painted a pretty appealing picture for me. You can probably guess how my plan had started to change by then. Then there was the matter of what I’d be able to hold over her head to make her give in. I needed a way to see into her personal life somehow. Eventually, I settle on stalking around her house at night when my folks were asleep. The town wasn’t very big, so it didn’t take me long to make it back to my own house in time, which came in handy on the first few night when I wouldn’t find anything useful. Nights like tonight, in fact. It was early in December and almost cold enough for me to see my own breath, so I was dressed in my warmest piece of clothing at the time, which was just a mildly tattered grey hoodie. Not what I’d wish for on a night like this, but it could’ve been far worse. On my way back, I was about to pass by an old party store when someone I knew from school walked out the front entrance.
It was the local “Goth Girl”, Sarah. She froze when she noticed me coming closer and gave an uneasy wave before calling out to me in an anxious voice.
“Oh, hey David. Weird running into each other outside of school, huh?”
She was smiling, but I could tell she was nervous. And I knew why as soon as I looked to her left. In her left hand, she held an unopened bottle of liquor. My reply was accompanied by an amused grin as I stepped closer again.
“Only in situations like this. Gotta be honest, I’m kinda glad to know I’m not the only delinquent in this boring little town, you know?”
I motion to the bottle with a nod, and her smile faded. She looked down at the liquor, then back at me with a worried expression on her face.
“You’re not gonna tell anyone, are you?”
I tilted my head to the side with an unsettled look, as if I was unsure of my own answer. I involuntarily dropped my facade and giggled when her worried expression grew worse.
“No, Sarah, don’t worry. You and me are cool. Not like you’ve ever snitched on me. Stay careful out here though.”
Her expression softened into a more genuine, easy smile and she chuckled right along with me. She was actually a friend of mine, believe it or not.
“Thanks, man, my parents would kill me if they ever caught me with this. How’s your sister doing, by the way?”
“She’s been doing okay recently. Still having trouble settling into the new routines, which has us all kinda worried. Kind of expected that though.”
We fall into step together and she gives me flashes me a sympathetic, look, which is then replaced with a reassuring smile, spreading across her pale lips.
“That’s pretty common with autistic people though, isn’t it? You guys have only been in town for eight weeks. I’m sure she’ll be fine later on, these things just take time. Besides, she’s got you looking after her at school, right?”
I return her smile with one of my own and sling an arm over her shoulder as we walk, cutting through the wooded area near the store to avoid prying eyes.
“Yeah, she certainly does. Thanks for the pep-talk, Sarah. It always helps.”
“Anytime, David. Us weirdos have to look out for each other, don’t we?”
We both let out a laugh at that and kept walking a bit longer until she saw her house coming into view. She said goodnight and picked up the pace to her house while I did the same, heading to mine. I definitely had a thing for that girl. Sarah fits the profile of what I’ve heard people call a “Perky Goth”, which basically means she’s more friendly than her dark appearance would lead someone to believe at first glance. Her skin was pale, almost to the point of being ghostly, but I liked that. Her pale complexion fit pretty much perfectly with the dark brown hair framing her face. Her eyes were emerald green and she often wore sexy black lipstick. Her figure was nothing to scoff at either. She was slim, but athletic in build and had just enough meat on her in all the right places. For anyone who’s onto the horror movie scene like me, her figure is pretty similar to that of a young Katharine Isabelle. She took that as a compliment when I told her as much. For anyone who doesn’t know who that it…oooohhhh, boy.
Now, I’m reasonably sure that some of you are wondering whether or not I’m planning to target her at some point. I’m not. The reason for that being that she’s never been bitchy to me in any way, not in comparison to the other girls. She turned me down politely when I asked her out two weeks ago as well. You see, if I make a move on a girl, and she turns me down nicely, I’m usually completely fine with that. If she’s cool about it, I will be too. It’s only the people who are blatantly hateful towards me or my loved ones that end up on my “radar”. People like Miss Wells. Speaking of her, my chance to finally get some dirt on her came at an unexpected time. It was the day after my last attempt at spying on her, and the school day had progressed much like any other. Still kept mostly to myself, save for the fun conversations with Sarah during our lunch period, got my work done, and waited patiently for the release bell to ring. I had to stay a bit later than the others though, I’d gotten a virus on my assigned computer and had to make up some overdue reports. When I was done, I walked out and took the usual route to my house, which involved me passing through the parking lot. Then the sound of some guy moaning caught my attention. Mumbling confused obscenities under my breath, I turned to face where the sound was coming from.
Several yards away from me, I saw what looked like someone on her knees in front of an old man next to the old blue Honda Miss Wells drove. As you can probably guess, I crept closer, smiling and pulling out my phone as I ducked behind another car. There Miss Wells was, kneeling in front of the school custodian with his dick in her mouth. She was sucking the upper half of his shaft while firmly stroking the lower half, her other hand playing with his balls. Neither of them saw me as I crept closer still and zoomed in with the camera. It was only a few seconds before the custodian came in her mouth, a string of it dripping down her chin when she pulled away from him. She swallowed the rest though, and was visibly smiling as she stood. My golden opportunity caught me by surprise, and I couldn’t have been happier about it. I’d re-watched the video several times later on that night, fantasizing about being in that lucky man’s place. I would be soon enough. I did plan to finish kinda differently though. Two days later, I had another overdue report to get finished and, as luck would apparently have it, I’d overheard that Miss Wells had to stay late as well. That was my window, and I surely wasn’t gonna waste it.
After I finished my work, I made my way to her classroom, sliding the door open and seeing her organizing several papers, mostly assorted U.S. history tests that hadn’t been graded on time. She didn’t seem to notice me coming in until I was just four feet away from her desk, at which point she looked up at me with an annoyed look several of her students had seen quite often by now.
“What the hell do you want, David. I’m pretty busy here, if you can’t tell.”
“Though teachers weren’t allowed to use that type of language at during work.”
I replied, almost smugly and with thinly-veiled contempt. In response to my comment, she just smirked and began to motion around the room with her free hand, the other one still scribbling away at the papers crowding her desk.
“You see any higher-ups or cameras in here, boy? Because I sure don’t.”
I shrugged, having to force my own smirk to remain hidden for now. That remark would bite her in the ass shortly. I figured now was as good a time as any to get to the point, and I still had a schedule to keep at home.
“You seem a little more bitchy than usual today, Miss Wells. Have a falling out with your old friend or something?”
Her cocky expression turned to one of surprise and anger at that. She stood up from behind her desk and sat the papers aside, her eyes never leaving my face as she stepped closer with her arms crossed. Her voice was low and angry.
“Excuse me? You wanna repeat that?”
“No, not really. What I do want, however, is for you to change your tone.”
Her hard gaze was fixed on me as I pulled out my phone and selected the video I’d taken of her with her “friend”.
“Unless, of course, you’d be fine with me showing this to the principal.”
She looked less pissed and more confused at my vague threat, until I pressed play on the video and turned the screen towards her face for her to see.
“How the hell did you get that!?”
She nearly shouted the question. If the school wasn’t otherwise deserted, her raised voice would’ve had me worried about getting caught quickly.
“Only got it because you were dumb enough to suck someone off out in the open like that. Can’t imagine that’s behavior the school would smile upon. Probably not the police either, that probably counts as public indecency.”
The anger faded from her face and was mostly replaced by fear. That was fun to see on her. I always found it funny, in an admittedly sick way, when I saw fear on some arrogant bitch’s face. Especially when I was causing it. What excited me more, however, is that the look, coupled with her lack of any comebacks, all but confirmed my victory. She shook her head sadly and lowered her gaze to the floor. To my mild surprise, her next words came out in an obviously defeated tone. It shouldn’t have surprised me, since it wasn’t the first time I’d done this, but it could still catch me off guard when someone’s massive ego broke and their attitude completely shifted.
“Please, don’t show it. I can’t lose this job, not over something like this.”
“Yeah, well that’s your problem, not mine. Maybe I’d be a little nicer if you hadn’t been such a bitch to me and my sister. Sadly though, you’re gonna have to earn my silence on this one.”
Miss Wells huffed, her anger clearly rising yet again, as she lifted her head to look me in the face.
“And how would I do that?”
“Your gonna be a nice little slut for me. Now, take off all your clothes, I want to get a good look at my new property.”
Referring to her as my possession gets her visibly angrier, but she steps back at begins to undress. Unbuttoning her pantsuit, her perky tits become less constricted, sticking out more as she begrudgingly throws the jacket aside. Then she unbuttons her shirt itself, opening it to reveal that she’s braless. As I said before, she doesn’t have the biggest breasts in the world, but they fit her figure pretty well and look just as form as I thought. When she goes to push down her skirt, I stop her.
“Turn around, I want to see your ass when you push your skirt down.”
She rolls her eyes, but does as she’s told. I sit on one of the desks and lean forward, almost right in front of her ass while she pushes the garment down, her red lace panties with it. I’m not ashamed admit that I’m an ass guy, a nice ass is a turn on for me. And I must say, it’s her best feature. I can’t help myself, I reach out and grab her cheeks with both hands, squeezing them firmly. She stumbles in surprise, but steadies herself. She looked back at me momentarily with an indecipherable look, but turned her head away when I faced her.
“You really do have a fine ass, Miss Wells. Can’t say it’s a mystery why that old man went after you.”
Several moments tick by with no response from her, which isn’t what I was hoping for. Blackmail sex is no fun if there’s no resistance involved. In hopes of getting a reaction, I bring a hand down on her ass, the sound of the slap resonating through the room. She cries out in pain and surprise, and I slap her ass a few more times until her cheeks are a light shade of red. She can’t hold her young at this point, apparently.
“You little bastard, I’m gonna–“
I also her ass sharply, effectively cutting off her oncoming threat.
“You’re gonna do what, exactly? I don’t think you really get the reality of the situation. I own you now. You have no rights to anything now as my slave, least of all your freedom of speech. You keep giving me problems, and that video will be everywhere before sunset. Or maybe I’ll just whore you out to some of your other students. How’s that sound?”
Several emotions flash across her face, including the strong hunt of humiliation when at the thought of me selling her to the very students she belittled with little to no real reason.
“Do what you’re told, and you’ll only have to worry about pleasing me.”
She looks conflicted, but hangs her head in defeated soon enough. That’s almost my favorite part of this little game of mine. With everyone I’ve blackmailed, be it for sex or just payback, it’s always satisfying to seek out their strong points and break them down. It makes me feel like I’m winning, and there aren’t many things in this world that feel better. Smiling once more, I rise from the desk and make my way towards her’s, settling into her chair and motioning for her to approach me. Reluctantly, she does. Her breasts giggling slightly with every step she takes, which makes it quite difficult to look away from them.
“Now, sit on my lap and start grinding that sweet ass on my cock.”
She slowly turns around and lowers herself onto me, steadily grinding away. After a few moments of this, I reach around to her chest and take a tit in my hand, fondling it as she keeps grinding. My other hand joins in, almost by automatic, and I pull her back to lean against me. After pinching both her nipples between my index and middle fingers, I whisper another command in her ear.
“Now your gonna straddle me and grind that cute little pussy against me.”
She gets up and turns around, blinking away years as she gets into position. When she starts grinding, I take one of her tits in my mouth, running my tongue over the nipples while still fondling her other tit. My free hand makes it’s way down her back and picks up where it left of on playing with her ass. My dick’s been hard since I showed her the video, but this “foreplay” still excites me. The sound of her softly crying helps too. I keep tormenting her until my arousal is too strong to hold back, at which point we can get to the good stuff.
“Get on your knees and take out my dick. That shouldn’t be hard for you.”
She shivers in disgust as she stands up, only to sink to the floor again. The way she’s looking up at me makes it pretty clear that she’s dreading what comes next. I get the feeling she’ll need some extra incentive for this.
“Take my cock out and give it a good, thorough licking. Do a good job and I won’t screw you today. That’s good motivation, isn’t it?”
She weakly nods, taking her eyes from mine, and pulls it out, her eyes widening in surprise at it’s large size. When she hesitates again, I grab the base of my dick and rub it against her face. She tries to pull away, but my hand on her head keeps her in place.
“And I mean really good. I better feel like you’re worshipping it with your mouth. Now get to work.”
She shuts her eyes and exhales. She parts her lips and starts running her tongue along the length of my shaft, sending little lightening strikes of pleasure throughout my entire body. I don’t even try to hide my amusement as she pleases me, and it’s not long before my shaft is fully coated in saliva.
“I’m sure you know what I want now, Miss Wells. I’m dying to see just how talented that mouth of yours is.”
She lets out what sounds like a growl at that and looks up at me again with anger in her eyes. Anger isn’t something I want to see in a slave when she’s about to put my dick in her mouth. I slap my dick against her face when she gives me the look. When I see the look of surprise on her face quickly turn back to anger, I do it again even harder. When she feels the precum I’ve smeared on her face, it seems to reduce her back to tears.
“I’m not giving you infinite time on this. Start sucking me off or I’ll you over your desk and go balls deep in–“
My threat is effectively cut off when she sucks me inside, taking my whole cock inside her mouth within seconds. I wind my hands in her hair when her nose starts to press against my pants, savoring the feeling of her throat constricting around me. When I let go of her head, she slowly pulls back, continuing her strong suction all the way back to the tip and releasing it. She lowers her head to the base and slowly runs her tongue upwards, swirling it around the sensitive tip before taking me in her mouth again. I grab onto her and manually bob her head until she starts gagging. Once I’ve let go, she pulls back to breath momentarily, then continues her work. Similar to the video, she sucks the upper half of my dick while firmly stroking the lower half. It feels absolutely devine and I vocalize my pleasure quite graphically. When I feel myself getting closer to release, I push her head back until my rod pops out of her mouth, staring intently.
“Keep stroking, and keep your eyes on me. Close them at any point, and you’ll wish you never thought to.”
The next look she gives me is the best one since this all started, an incredible combination of humiliation and disgust when she realizes that, not only am I close, but I already have a target in mind. I manage to smirk at her just before my release hits, and all I can do is watch and moan as thick streams of my release land on her beautiful face. It feels like an eternity until I’m done, and it might as well have been considering how much of her face is covered. It was no small release, and I’m left drained of energy. I rub the head of my rod against her lips as I look down at her, smearing a white, gooey smile onto her face. Her face is more or less emotionless, but you can a lot of emotion in her eyes. She’ll never forget this. Neither of us will. I take some pictures of her face and body and make her tell me “thank you” for the facial before I put my cock away and leave. This was more enjoyable than most of my previous victories, and I’m definitely going to make the most of this one. But now, I’ve got chores to do at home, which are easier to focus on after having my needs tended to. The night ends with me and Millie playing “Batman: Arkham Knight” together in the living room. It’s her favorite game, mostly due to the lore, and I’m feeling pretty generous at the moment. She’s not great at actually playing it, but she has me to give her pointers. I can’t help but laugh internally at how I can be so sweet to Millie after something like this. I’m just glad she doesn’t know.