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Glee - Blackmailing The Gleeks	By : Perversity Category: G through L > Glee Views: 28902 -:- Recommendations : 1 -:- Currently Reading : 0
Disclaimer: I don't own nor do I make any money from this story or anything related to Glee.

Chapter List
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I would like to make something perfectly clear before we start. This story won't be for everyone! It doesn't contain any hardcore fetishes such as scat and stuff, but it's also not going to be all happy and fun either. If you've read my other story, you pretty much know what to expect. The biggest difference between the two is that the character in this story is the exact opposite of the last, sexual experience-wise. At the beginning of this story he's a virgin and learning the ropes, while in my other story the main character was intelligent and very experienced.
My stories focus on emotional and psychological torment, not physical. This character, just like my previous one, doesn't believe you should have to physically hurt someone when you can achieve the same or better results by manipulating them and giving them pleasure. So please, if you're into something light hearted then go elsewhere, and vice versa if you're looking for a hardcore rapefic then this isn't for you.
The first chapter is kind of rough. The second chapter will focus more on the pleasure rather than dominance. I was the Master in a BDSM relationship for years with a very dear friend of mine. She got off on humiliation and degradation instead of pain, so I'm going to incorporate a lot of what I've learned into this story.
I enjoy all criticism, as long as it's constructive. If you have something to say then please say it.
I hope you like the story.
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Chapter One - The First Step
You know, I’ve always been a geek. I play video games, watch anime, and I do great in school. I have absolutely no sex life, mostly because I don’t converse much and I have few friends. I keep to myself and more or less ignore anyone who tries to bother me. It’s not like I don’t want to connect with people, I’ve just never had the patience to learn how. So when the ex-cheerleader, Brittany, starts reluctantly pumping her right hand up and down my shaft it’s an incredible feeling.
Brittany is pretty much the school slut, so getting her into bed isn’t really what one should consider an accomplishment. The true accomplishment is the fact that she has no choice in the matter. Well she has a choice, but doing anything other than what I say could possibly ruin her best friend’s life.
I take great pride in being unnoticed, it lets me listen in on things people want to keep secret. In this case, the blond cheerleader’s best friend, Santana, is a closeted lesbian. In high school, it’s kind of important to keep that stuff private. It’s a little sad how being a slut is considered better than being a lesbian, but that’s just the way it is. At first I didn’t really care. I’m a very open minded guy, and I don’t care what people do with their lives as long as they don’t hurt others.
But as I was looking up porn one night, I came across a video that included a blackmail scenario. It had really bad acting of course, but it planted the idea in my head and wouldn’t allow me to think of anything else. So I watched more videos and read stories, the ideas of what I could do with the information I had almost too pleasing to think about.
Just for fun, I started writing down my ideas, planning what I would do if I wanted to blackmail Santana into having sex with me. But no matter what I came up with, I kept hitting a wall. Santana is pretty shameless but still full of pride. If I tried blackmailing her she just might publicly out herself and get me arrested. So I added her best friend to the equation.
There are already rumors that Brittany and Santana have had sex before, although no one has any real proof. It always seemed like some stupid fantasy the guys thought up. However, with the information that Santana is a lesbian, it’s far more likely to be true. I’ve been able to catch tiny snippets of conversation between those two when passing them in the hall, and if I had to guess I’d say those two are a lot closer than even a sexual relationship would imply.
Brittany is pretty dumb, but she’s also incredibly loyal, especially to her best friend. Deciding to think of my conquest of Santana as a multistep process, I decided that the best solution would be to use the blackmail material on Brittany instead, and then use both the information and Brittany against Santana to make sure it stuck.
I’m normally a nice guy, so the idea of doing all of that was certainly out of my element. But the thought of having sex with not one but two cheerleaders made me abandon all of my doubts and take the chance. I’m glad I did.
“Come on! You’re not being very enthusiastic right now. I guess you don’t care about her as much as I thought.”
The taunt does the trick and she moves her hand faster, shooting little jolts of pleasure up my spine. It’s my first sexual experience, so I’m very sensitive. I struggle to keep my mind clear and watch her face as her fist rapidly pumps my shaft. She’s biting her lower lip, while her eyes try to focus on anything but me, which is a little difficult because I’m actually pretty big in that department.
Not wanting to release too soon by watching too much, I look around the room we’re in. It’s an old classroom that isn’t used for anything more than storage these days. Various boxes litter the room and the light hasn’t been changed in some time, casting a half-dead glow over the area. The sun is starting to set, most of the students having already left for home, but the occasional footsteps can still be heard out in the hallway.
During the sports season this room actually sees a lot of activity, but it’s not unusual for the room to remain unused for weeks at a time. For Brittany, every sound in the hallway makes her nervous, causing her to turn her attention to the door every few moments while her hand jerks me off. For me, it’s a little thrilling to be getting a rather nice handjob from a popular cheerleader at school. The danger of getting caught makes it so much more exciting.
“I knew you’d be good at this. Now start using your tongue. I’ve heard rumors that you can get a guy off multiple times with just your tongue and I want to see if that’s true.”
Her fist stops moving, and she looks up at me with pleading eyes. I’m not going to lie; it really is difficult to be the bad guy when it’s not in my nature. Brittany has been “off the market” for some time, much to the dismay of some of the guys who had sex with her. She has a steady boyfriend whom she really seems to care about, and here I am forcing her to cheat on him. It sucks that she’s collateral damage in my attempt to blackmail Santana.
But looking down at the beautiful blond with her hand still wrapped around my shaft, and that pretty face just an inch away from it, makes it impossible to ignore my base desires. I move my hand to the back of her head and pull her closer, pressing my hard shaft against her face. She tries to pull away but I hold her in place, making her feel the heat of my cock against her skin.
“You don’t only have your best friend to worry about here. You know how quickly rumors spread in this school, considering how often you’ve been a part of them. If someone were to spread a rumor about you giving a guy a blowjob at school, how long do you think it will take for your boyfriend to hear about it?”
I grip the base of my cock and slap it against her face, making her flinch and close her eyes, looking truly miserable and on the verge of tears. For some perverse reason, that only excites me more.
“Your boyfriend may care for you very deeply, but do you think, considering your reputation, that he will believe you over the rumor? And even if he does believe you, he’ll have his doubts. He’ll wonder if you are still the slut you were before. Doubts can erode trust very quickly. Now, decide which is the lesser of two evils.”
Her eyes open and she gives me a sad look, but when she opens her mouth and circles the head of my cock with her tongue, her choice is pretty clear. The feeling of it hits me like a truck and I groan almost too loudly in reaction. I clench my teeth to muffle the next groan when she licks the tip of her tongue just under the head.
I have nothing else to compare it to, so I don’t know if she’s good or not, but it still feels incredible. When her tongue licks up from the base of my shaft circles around the head again, I wind my hands in her hair and pull her closer, demanding more from my reluctant partner. I focus on her again to watch her lick every inch of my shaft, making sure no part was left unattended to.
“I guess the rumors are true. I must say, your boyfriend must really love you. If he can experience your talented tongue all the time and not think about how you became so good because you practiced on so many others, then he really cares about you.”
I have no idea why I’m tormenting her, but I can’t really stop myself and the sudden tears in her eyes thrill me immensely. Despite the incredible amount of guilt and shame she must be feeling, she continues to work her tongue all over my shaft. My groans only seem to make her feel worse, but still she continues. I guess she figures that as long as her boyfriend doesn’t find out about this, then it won’t hurt him.
I have a lot of pride in my self-control, but the sensations are starting to wear me down. Every lick is making my entire body tense up in pleasure, and my balls ache with the demand for release. But I desperately hold it back, struggling to maintain control so I can push things even further.
“Good girl. Now give me one hell of a blowjob. You’ll be one of my first, so make sure to leave a good impression.”
She closes her eyes and leans forward, her hot breathe enveloping the head just a moment before her mouth does. As her lips close around the head, my hand in her hair tightens and I can’t help but push further, making her take more of me inside her mouth. I regain control of myself when she chokes and I loosen my hold on her, allowing her to control the blowjob.
She immediately backs up and slides my cock out of her mouth with a slight pop to pull in oxygen. She looks up at me and I lock my eyes on hers as she takes me in again, closing her lips around the head and sucking on it. The sight of her lips stretching to accommodate my considerable size is almost as good as the feeling itself.
It’s almost disturbing how quickly I start to lose control over myself. I try to reason that I’m just a virgin and this is my first sexual experience, while Brittany has been doing this a lot longer, but I can’t help but feel ashamed of my lack of control. I’m certain it will improve over time, but I’m still not pleased about it.
“Tell me something, Brittany. Is it true that you’ve fucked most of the football team?”
She closes her eyes again in shame but slowly nods. The fact that she’s doing it with half my cock buried in her mouth sends pleasurable sensations up my spine, making it difficult to think clearly.
“Are you ashamed that you were so easy to get into bed? I mean, you’re known as the school slut. Most of the guys in this school only want to be with you because you’re a sure thing.”
She nods again and I smile down at her. I know she’s been trying to change and move on from the type of girl she used to be, so reminding her of all that is no doubt causing her a lot of inner torment. I suppose she has learned what kind of relationship she can have with a guy who genuinely cares for her, and she doesn’t want to go back to being the slut that everyone remembers her as.
But here she is, sucking off some guy in a storage room. She’s not doing it willingly, but the fact that I’m enjoying it so much is because of her vast experience with other guys. Tears slide down her cheek and it doesn’t help when I tell her to keep sucking. She immediately starts bobbing her head up and down my shaft, keeping up almost continuous suction.
I slowly reach the back of her mouth and butt up against her throat. Not even needing to tell her to do it, she starts to swallow me down her throat. The feeling of it nearly sends me hurtling over the edge, and I have to run a bunch of non-sexy images through my mind in order to prevent myself from blowing my load right then and there.
She finally stops about a couple of inches away from the base of my shaft and stays still, working her throat muscles around my cock. That is way too much for me to handle. I once again tighten my grasp in her hair and hold her in place, only pumping my hips a couple of times before I finally release my pent up semen down her throat. She only briefly struggles against my grip, trying to rise up and off my cock, but she quickly has to divert her energy to swallowing each spurt of cum that slides down her throat.
It’s the hardest I’ve ever come in my entire life, and my mind blanks completely as I force her to drink every drop. When she swallows the last of it, my grip on her hair loosens and she immediately pulls back, gasping and coughing for oxygen. I stare at the blond girl for a while until I am able to focus again. My cock softens very quickly and I know that even if I want to, there’s no way I can go another round after that. Not yet anyway.
“Are we done?”
Her breathing is under control, but her voice is hoarse. For some reason, it pleases me to know that she can hardly talk right now because of me.
“For tonight. I’ll contact you tomorrow and tell you where to meet me.”
She can’t possibly think this is going to be over after just one blowjob. You would think her experience with men would show we’re definitely not satisfied with just a blowjob when we can get more than that. There are a lot of things I want to do to my new sex slave before I bring Santana into this. I need her under my full control before I take the next step.
“You should probably go and spend the night with your boyfriend. After tomorrow, you’re going to have a lot more to feel ashamed about.”
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Glee - Blackmailing The Gleeks