Glee - Blackmailing The Gleeks

My fellow perverts, I will never try to deny that I’m a little screwed up in the head. It’s been a week since I finally enslaved Santana, and juggling two girls, one of whom doesn’t even know about the other, is a real chore. A chore that’s well worth it, if I do say so myself.  I alternate between the two every day, and torment Santana with the knowledge that I’m fucking the woman she loves when I’m not with her. That is generating a smoldering level of animosity toward me. Since she can’t satisfy her desire to pummel me, it’s coming out when we have sex.

There is nothing gentle or slow about what we’ve been doing all week. It’s rough and at times borderline painful, but never quite reaching violent. She’s very aware that her only outlet for her anger towards me is also pleasuring me immensely, which doesn’t help her attitude at all. So she’s pretty much in a no-win situation and the only thing she’s getting out of it is one powerful orgasm after the next. To put it simply, we’re using each other and I’m experiencing the most intense sex of my life.

But don’t get me wrong, I’m also enjoying the slower, far gentler sex with Brittany. With her I can just take my time and enjoy a slow build up to release. And whenever I can, I record these sexual acts, getting every sordid experience on video. It’s gotten to the point where I’m pretty secure in my control over them and it’s about time I move on to the next phase, which unfortunately includes letting Brittany know about Santana.

My main method of control over her was my threat of outing her best friend, so there’s no telling how she’ll react when she discovers her sacrifice was more or less for nothing. I knew I had to think things through very carefully and delicately plan a way to let the blond know while minimizing any risks. After a full week to think about every little detail, I came up with the perfect idea. The result of that idea is Brittany walking into her room and catching Santana deep throating me on her bed.

Okay, so maybe I define subtlety differently! The Band-Aid is now off, and that’s all that matters in the end! The absolute best part is that I didn’t tell Santana about it at all, so when the blond cheerleader walks in on us, she has half my shaft down her throat. The sight of Brittany startling her, she tries to rise up off my cock but I stop her with my hand in her hair, holding her in place. I look over at the stunned blond and smile.

“Hello, Brittany. Get over here and get on your knees. Now!”

She responds almost automatically to my firm command, I’ve been training her for a full month after all, and joins her best friend on the floor in front of me. I let go of Santana but before she can pull herself off I fix her with a glare.

“Keep sucking. If you stop at all then I’ll make her take your place.”

The glare she shoots at me could melt steel, but she does as she’s told and starts bobbing her head again. Although I’m able to react calmly, it still takes a lot of effort to talk. Santana is almost mind-numbingly good at sucking dick, and she’s only gotten better from all this practice. After I make sure that she’s going to continue pleasuring me, I return my focus to Brittany.

“Allow me to give you the nutshell version, Brittany. I told your best friend about how much you’ve sacrificed to keep her secret. Because she cares about you so much, she agreed to become my own personal sex slave, just like you. She’s the main reason why you’ve had every other day to yourself for the last week. She takes care of me when you can’t.”

Throughout my explanation, Brittany stares at her best friend in surprise and not a little bit of sadness. She was following my orders to keep her best friend safe, after all. She’s been forced to cheat on a boyfriend who adores her, and I’ve taken no small amount of pleasure in making her feel like the slut that she’s been trying to change about herself.

“But she hasn’t been entirely unwilling. Get this girl angry with no outlet and she’ll fuck your brains out. It’s kind of touching what people will do for love. I’ve fucked her even harder than I have you, Brittany, and she keeps coming like she hasn’t had a good lay in years. Look at her now, sucking my dick to protect you, while just yesterday you were doing the same to protect her.”

Tears began to stream down Santana’s cheeks and she stops moving, so I take her head in my hands and start moving her up and down my cock. I purposely let out a loud moan as her nose presses against the base of my cock. Brittany is getting visibly more and more upset watching her friend do this and looks up at me.

“Why are you doing this?”

I laugh in response and then finally slip my cock out of Santana’s mouth, allowing the girl to breathe as I smile down at them.

“Part of it is because it feels good. You’re both incredibly hot and really good in bed. Up until just over a month ago I didn’t have any chance with either of you, but now I get to fuck you whenever I want.”

I reach down and slide my hand beneath Brittany’s shirt, running my fingers down her smooth stomach then back up to squeeze one of her bra covered nipples. Brittany is the kind of girl who is always horny, so you can get her started with very little effort. I look over at Santana, who is clearly not enjoying the sight of me touching the woman she loves. Knowing I’m doing it is one thing, but watching it is quite another.

“But the main reason is because of her. People who are afraid to be what they really are piss me off. If she’d been open about her sexuality right from the start, I never would have found the leverage I needed to begin all of this. Now it no longer matters, because I have enough material on the two of you to ensure an entire lifetime of sexual slavery to me. I’m a horny teenage boy with two smoking hot cheerleaders taking care of my needs; of course I’m going to make use of you.”

Pulling my hands out of her shirt, I order her to remove all of her clothes and get back in position, then watch her do so while I rub my shaft against Santana’s face. My eyes are drawn to the athletic blond, and not for the first time I admire her body as more of it is exposed to me. When her clothing is removed she drops to her knees between my legs again and I slap my cock against Santana’s face once more before pressing the tip against Brittany’s mouth.

“Go ahead and show her how good you are.”

Brittany hesitates and looks at her distressed best friend. It’s clear, to me at least, that the last thing Santana wants to do is watch the woman she loves pleasure me. The blond turning back to me and sucking the head of my cock inside her mouth is a good way to remind her that there is no real choice in the matter. I look down into the blonde’s pretty eyes and groan as she takes most of my cock down her throat within just a few seconds.

The tears are flowing from Santana again, but I place a hand behind her head and pull her closer until her cheek is pretty much rubbing against her friend’s, getting the perfect view of her pleasuring me.

“I’m sure I don’t know to tell you this, Santana, but Brittany is way too good with her mouth. Even if I only used her mouth every day, she would still drain me dry. There’s just something about her that makes it so much fun to watch her do it too. She’s probably spent more time with my cock inside her mouth instead of her pussy.”

I know I’m tormenting them both, but Santana even more so. It’s immensely satisfying to look down and see both my girls on their knees before me. My arousal keeps shooting through the damn roof and I struggle to maintain control over myself.

“Help her out, Santana. The sooner I come the sooner you get to stop watching her pleasure me.”

I let go of her head and allow her to move, then nearly embarrass myself and come immediately when the dual sensations of one mouth around my cock and one licking my balls makes my entire body shudder. Pulling on some deep, lesser-known reserves of willpower I somehow manage to hold off, but having two skilled mouths pleasing me keeps me right on the edge.

Without even needing to tell them to, they suddenly switch and Santana’s mouth deep throats my throbbing shaft while Brittany changes tactics and sucks on one of my balls. Without any previous experience with a double blowjob, I literally have to fight my body to prevent my release. Despite my constant moaning and shifting, I don’t take my eyes off the girls, instead making sure they know I’m watching.

“Stop sucking, both of you just use your tongues. When I tell you I’m about to come, one of you better have your lips around my cock ready to suck it down.”

I can’t help myself; I’m experiencing every man’s fantasy right now. They immediately do as they’re told, but they both have a small look of determination. Both of them want to stop the other from being forced to swallow my semen, so they’re both going to try. Neither of them wants to, but both of them will try. I won’t lie, at this moment I love my life.

Having two very talented tongues on my shaft nearly makes me hyperventilate. They both take turns running their tongues up and down my cock, with the one waiting circling her tongue around the sensitive head. Knowing that the person who wins will have a much likelier chance if she’s closer to the tip of my cock, I wait until Brittany is licking the head before I warn them. Santana isn’t nearly fast enough and in a split second, the blonde is shoving every inch of me down her throat.

I manage to smirk down at Santana and wind a hand in Brittany’s hair, holding her down on me as I moan loudly and come down her throat. She already has plenty of experience with this, and expertly swallows my semen and milks my shaft. Santana watches as her best friend’s throat expands while she drinks down every drop.

I feel energy leave my body with each shot of come, and when I finally stop I pull Brittany off my cock and struggle to pull in oxygen. While resting, I quickly think up the next part of my plan. To be honest, and I know I’m going against my golden rule here, I didn’t entirely think the next part through. Despite everything I’ve experienced over the last month, it’s completely new to me.

But it’s necessary to my grand scheme if I also want to bring another person into this.

“Santana, lay back on the bed and spread your legs.”

I guess she incorrectly assumes I’m going to fuck her instead of Brittany, because she obeys without complaint. When her head rests on the pillows I stand up and push Brittany onto her hands and knees at the edge of the bed, actually not too far away from Santana.

“We’re going to play a game. You see, Brittany has told me a lot about your relationship over the last month. Fascinating stuff, really. I especially liked the part where she told me that the person who took her anal virginity was you.”

I absentmindedly rub my hand against Brittany’s firm, lovely ass and smile at Santana.

“Not only that, you’re the only one who has ever taken her anally. It’s like your own sacred spot, a piece of her only you can ever have. I genuinely think that’s kind of sweet. You both sleep around but you reserve something that’s just for the two of you. I like that, as weird as it is. Another surprising detail is that you haven’t lost yours.”

Santana apparently doesn’t like where this is going, because she’s staring at me in disbelief, a slight shake to her head as she silently begs me not to do what I want to do. I’ll be perfectly honest with you, even the cold exterior I’m trying very hard to keep up melts significantly when I see the look on her face. I think I’ve mentioned this before, but I’m kind of a romantic. I can certainly understand wanting to have a piece of someone that nobody else gets to experience. I quickly revise the game in my head.

“So here’s the game. I’m going to fuck Brittany, there’s just no way around that. If she makes me come first, then I get to have your anal virginity and you get to have her ass all to yourself. However, if I make her come first, then I fuck her ass right here in front of you. Now here is where you come in. If you can make yourself come three times before I do just once, then I get to take you both anally, but she gets your anal virginity and not me. Of course, that only applies if she makes me come first.”

You can officially file me under “Right Bastard” and be done with it. The original plan was just fo fuck Brittany anally and put her in a position where she’ll need to make me come in front of Santana so I won’t take her best friend’s anal virginity.

With these new rules, Santana can only aim for an outcome that results in me having both of them. The last thing she wants if for me to take Brittany anally, but she also doesn’t want me to have her anal virginity either. To get even a little bit of what she wants, she’ll have to sacrifice her virginity to me or sacrifice Brittany to me. I’m not an idiot, she’s a woman in love. If Brittany loses or wins, either way, the outcome is a lot worse. However, if Santana manages to win, then she gets something in the middle. Nothing great, but nothing terrible either. She has no real choice except to win this herself.

As for Brittany, she has even less of a choice. The only good option for her is to make me come first. Whatever the outcome, I’m going to have a lot of fun. I walk up behind Brittany and rub my shaft between her legs, brushing up against her sensitive clit. Her loud gasp seems to motivate Santana even more.

“Do you both understand the rules?” They both nod, “Good, now let’s begin.”

Wasting no time, I push forward and quickly bury my entire length inside Brittany’s tight pussy. I can never get used to how good it feels, or how erotic it sounds, when she grips my shaft within her and cries out sharply from the penetration. She seems stunned for a few moments and I’m able to pull almost all the way out and enter her deeply again twice before she remembers her role in this.

She braces herself against the bed and starts pushing back against me, her ass smacking loudly against my hips as she meets me part way. I’ve learned that Brittany loves just about everything about sex. She loves the sound of it, the groans and moans, of skin smacking against skin. She loves the feeling of losing control of herself and just bathing in the all-consuming pleasure of something buried deep inside of her. Get her started and she leaves the entire world behind.

I look up from the tantalizing view of her back flexing each time I push inside of her, and check on Santana. Without anything else to look at, and apparently finding it impossible to close her eyes, she has nothing but a view of the woman she loves getting fucked by me to pleasure herself to. Knowing she has to make herself come three times, one hand pinches and pulls on her nipples while the other hand furiously pushes two fingers in and out of her dripping pussy, stopping every once in a while to thumb her clit.

It’s one hell of an erotic sight, and when I notice that Brittany’s head is hanging down, I give her firm ass a hard slap to get her attention.

“Watch Santana pleasure herself. Don’t take your eyes off her no matter what.”

Not having even the slightest desire to disobey, Brittany raises her friend and stares at her friend, both of them getting a full view of each other’s pleasure. Santana looks sexy as sin masturbating, and I know from experience that Brittany’s facial expressions are always intense when she’s having sex.

Although I’ve always felt guilty getting Brittany involved in this, I can’t deny the fact that she’s one hell of a lay, and I would have been missing out if I had chosen not to include her in my plans. Even overcome with her own pleasure as I ram away at her, she clamps down around my cock each time I enter her and it’s almost tight enough to stop me completely. It’s the perfect way to milk my cock, and she knows how much it drives me crazy.

I have no intention of coming until Santana reaches her three orgasms, and the training I’ve done over the last month has given me the gift of being able to hold my release off for a while. Brittany has that ability as well when she’s determined, and right now neither one of us are close to blowing it.

I focus on Santana again when her moans reach a higher pitch and I watch her entire body shudder as she comes for the first time. I’m not worried about her faking it at all. Santana can do a lot of things, but she can’t fake an orgasm worth a damn, and trust me she has tried. I smirk when I notice that she doesn’t take her eyes off Brittany during climax.

Deciding to alter the angle of penetration, I bend forward and grab her swinging breasts in my hands, squeezing the firm globes between my fingers and tweaking her nipples.

“Oh shit! Ahh!”

Brittany curses loudly and then cries out as I ram into her, the new angle and extra attention to her body apparently quite welcome. She tightens around my shaft and closes her eyes, a hiss between her clenched teeth telling me she’s fighting off an orgasm. Not wanting to push her over that edge, I get her several moments to control herself before I start moving again, each thrust making the beautiful blond moan in pleasure.

I must admit, it’s insanely difficult for me to keep control as well. I have the added benefit of the earlier orgasm taking the edge off, but Brittany knows exactly how to pleasure me.

“Please, fuck me harder! I’m so close!”

Damn her! I’ve always enjoyed the sound of her voice during sex, and she knows that. Apparently she wants to torment me, even though we’re all aiming for the same outcome.

I watch as Santana fingers herself to another orgasm, now only one away. I try to laugh at her, but it only comes out as a cough when Brittany chooses that moment to beg me to come inside of her.

“As much as you claim to hate me for fucking Brittany, you really seem to get off on watching us do it.”

Santana glares at me, but it’s hard to take her seriously when she’s masturbating and moaning at the same time.

I suddenly straighten up and grip Brittany’s hips in my hands, then lift her up so I can push her fully onto the bed. When I’m done repositioning her, her face is only a few inches away from Santana’s. Not wanting to break the pace any longer, I resume ramming my way inside of her.

Brittany can’t hide her pleasure even if she tries, and when she opens her mouth and lets out a loud groan, Santana takes that opportunity to lean forward and kiss her. Santana’s right hand moves up behind the blond’s head and pulls her into the passionate kissing, eliciting a moan from the surprised, but happy cheerleader. Her other hand speeds up between her legs, quickly approaching her third orgasm.

Not wanting to disrupt the kiss, and to be honest I don’t hate the view, I slow down my pace so her entire body doesn’t move with the impact of my thrusts. It’s not long before Santana finally reaches orgasm again, whimpering into Brittany’s mouth as her entire body shudders. The sight of the two cheerleaders kissing, not to mention the sensations I’ve endured so far tonight, I can feel my own release right on edge of a long cliff.

When Santana pulls out of the kiss, Brittany lets out a long moan and shudders, but manages to hold off her own climax somehow.

“I love you, Brittany.”

I barely hear her whisper it, but Brittany smiles at her friend.

“I love you, too.”

Perfect!

The fact that I need to come right after such a nice moment is purely coincidence, but I don’t hear any complaints. I grip her shoulders in my hands and pull her back as I push forward, non-too-gently burying my cock inside of her as deep as I can and shooting my semen inside her body.

Brittany curses loudly in response and her loud moan signals her own release, her entire body convulsing as pussy ripples around my shaft, milking me of every drop I have. I knew I wouldn’t be able to try anal sex that night, but I have plans for that later.

When we both finish coming, I pull out of her and smile when she lays down beside her best friend to recover her strength. Taking in the sight of the two beautiful girls laying side by side, I almost forget the next part of my plan. It’s utterly impossible to completely forget it however, since there is picture of my next plan beside Brittany’s bed.

“Okay, you two have one last thing to do before I leave.”

I cross the bed and pick up said picture, showing it to the girls.

“I want you to tell me everything you know about Quinn Fabray.”

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It took a while, but here's the next chapter. I had some fun with this one, and pretty much used it as chance to bring Quinn into all of this. I already know how I'm going to do that, so the only thing I need to do is write it. The next chapter will focus on two things: Blackmailing Quinn. Brittany taking Santana's anal virginity. The buildup to adding Quinn has already been going on long enough, so there won't be any chapters between the blackmail and the sex.

I hope you liked this chapter, and if you did then please show that ratings bar and review section some love. Feedback really does help. :)