6 Times a Day

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William Osborne, Jesse Boyer

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After it was over, Alan sat on the stage. He looked around and marveled at his fate. How is it that it's come to this, that I can have sex with the entire cheerleading squad at the same time? I never even planned this, it just kind of came together piece by piece. I guess Janice and Joy are just kind of swept along with the current, but that's cool.

Heather wiggled about and moaned loudly, trying to get Alan's attention now that he'd climaxed. She thought, This is bullshit! Everyone here is going to pay, and pay dearly. They're all treasonous fucks, including Alan. They will rue the day they thought they could best Heather Morgan!

Looking around some more, Alan could see Kim felt slighted. An idea popped into his head. "Kim, don't worry. I still think you're great. It's just that I wanted to see how Janice was with titfucks. Tell you what. I've got a special surprise for you. I'll give you the details later, okay? But it'll be fun."

Kim's happiness bounced back. "Okay."

Joy seemed a bit miffed as well, though. She complained, "So, is that how it's going to be from now on? 'Girl, you go here, and girl you go there,' like we're all just here to please you?"

Alan pondered this question while taking his pants off altogether. Eventually, he nodded. "Yeah. Pretty much. Is that a problem? If you're not into it, I'm sure someone else would be, so it's not like I'm forcing you or anything. I'll bet Amy here wouldn't have minded taking the ass position."

Amy nodded enthusiastically.

Joy, still glum, said, "No, it's not that. Of course sex is fun. It's just that the way you did it seems a bit, well, cold. That's all."

"You've got a point there," he ruefully conceded.

He thought, She's quite right. It was cold. I climaxed, but nobody else even came close to cumming. And you know what? It's just not as much fun this way. I know it's key to remain dominant, but when there's no emotional connection and no attempt at friendliness, it's extremely cold. I think this is a glimpse of the future if "Bad Alan" takes over completely: coldness, cruelty, and domination. That's not me. I let my urge to cum take me over completely. I need to be solidly in charge, yet loving.

He said very sincerely, "Sorry. It's just right then I was in the mood to get off as quick as humanly possible. It's usually not like that. I promise my next time with you will be different and I'll make it up to you. But that's just it: time. I never have enough. Right now I've got to launch into this whole Heather thing because we probably have twenty minutes max, if there's going to be time to get back to shower and everything. I'm sorry... Are we cool?"

Joy smiled at his improved attitude. "We're cool."

He continued, "Can one of you take her gag off? Let's see how the bitchslut is doing. And let's get her up on a table so she'll be level with my dick."

Janice took the gag off and the others helped lift her up and put her face down on a nearby table.

However, Heather still didn't say a word.

Janice complained, "See what I mean? When we took that off last time, Heather cursed at us like a drunken sailor. But now she just stares ahead sullenly, like you lobotomized her or something."

Alan explained to Janice, "That's because she knows that's she's in big trouble and she doesn't want to make it any worse. Isn't that right, Heather?"

Heather turned her head in Alan's direction. "Sir, this is the lamest bunch of wanna-be, sorry-spanking, limp-wristed excuses for torturers I've ever seen in my life. Frankly, it's embarrassing! I think it's pretty obvious who the natural leader of the cheerleaders is and who the pretenders are." She added crisply, as if in the military, "Sir!"

Heather surprised herself by saying that. She'd been planning to issue dire threats to Alan and everyone else. But while she was being repositioned on the table, she got a good long look at Alan's flaccid penis and it was like she clicked into a different mode. Her pussy started to moisten and her mouth began to water.

Amy had been stroking a pair of dildos in and out of Heather's holes, but Alan now waved Amy away from her dildo tending duties. He grabbed the anal dildo and began stroking it in and out, mostly to test to see how easily it slid.

As soon as he took over, Heather started panting and groaning. The way he was working the dildo was absolutely no different from how Amy had been doing it, but Heather obviously got off on the fact that he was doing it. The idea of any of the cheerleaders controlling her in any way was a big turnoff, but the thought of Alan controlling her got her very hot.

Finally! she thought. What the fuck was the fuckhead thinking, wasting time with these skinny skanks? True, they're attractive, but everybody knows I'm in another league. If he's gonna fuck me, well, maybe I can delay my vengeance until he's done.

He removed the dildo from her pussy to make room for his dick. Then, taking the confident tone that aroused her so much, he asked, "So. Who IS the leader of the cheerleaders, my bitchslut?"

Heather was about to answer herself, as if there was any question, but then she stopped. She felt his newly revived erection sliding near her pussy lips even as he resumed working the dildo in and out of her ass, and that gave her pause. She tried to wiggle his erection into her slit, but in vain.

She felt a surge of joy upon being called "bitchslut." But at the same time, she felt extreme frustration that he was teasing her pussy. Shit! He's doing it again. He's fucking with my mind. Not this time, you fuck! Not this time! Ha!

He asked impatiently, "I said, who is the leader of the cheerleaders, bitchslut?"

Finally, she dropped her head and said, "You are, Sir." Her face turned redder and redder.

Fuuuck! Why did I say that? This is so embarrassing, with everyone listening. Stop, Alan, stop! Not now!

"And who is at the bottom of the 'list'? The lowest ranking out of all the cheerleaders?"

"I am, Sir." She didn't want to say that, but between the anal dildo and the way he was rubbing his erection directly over her pussy lips now, she felt all her self-control slipping away. It was all she could do not to shout, "Stick it in! Stick it in! Any hole, just stick it in!"

Janice punched the floor in frustration as she sat there. "Alan! See what I mean? How do you DO that?! She would never say that to any of us in a million years! If she did, it would threaten her head cheerleader position."

He replied, "Well, I hate to say this, but it helps to have a penis."

Janice and the others clearly saw the way he was using his stiff rod to drive Heather crazy, but she complained, "I know, but it's more than that. Her attitude changed as soon as you touched her ass."

"That's true," he conceded, while still pumping the dildo and teasing her with his erection. "I suppose that it's mostly about attitude. The problem is, you come in here thinking that she's the head cheerleader and how do you wrestle information out of her? That's the wrong approach. You need to KNOW that she's no head of anything. She's nothing but a cocksucking, ass-hungry bitchslut who exists solely to serve her Bitch Tamer's dick."

Heather couldn't help but moan with arousal as she heard that. She blushed, painfully aware of the other cheerleaders gathered around her. That sounds so fuckin' HOT! True, it's bullshit, but dammit, I don't care! But everybody else needs to get the fuck out of here. This is between him and me.

He went on, "She's the lowest of the low, a complete whore, except that she's lower than a whore because she's not even worth paying money to fuck. She has a nice body, true, but that's only because she was born and bred to be filled with hard cock and hot cum by the likes of me. Isn't that so, my bitchslut?"

"Yes, Sir," Heather answered, her face now burning deep red with embarrassment. Alan, don't tell THEM that! I'm YOUR whore. They need to go!

Janice tapped Joy, sitting next to her. "You see? You see? Friggin' unreal! If I said that same stuff, Alan, I don't think it would work. Hell, I know it wouldn't."

Alan pulled both dildos out of Heather, then stood up and walked around to her front, leaving her holes unfilled. "That's probably true. For one thing, you can't just say it, you have to really mean it in the moment. That's the key. Heather knows that I'm not just flapping my lips and I really, truly mean it. I KNOW that she's a slut, my slut, and that it's her duty to sexually service me. That's just a plain fact, isn't it, Heather?"

Heather wanted to cry because she was acutely aware of the others listening to every word. "Yes, Sir. But can't you ask the others to leave?" She begged him in her own mind, Please! Don't let them know everything! I'll never live it down!

"Bitchslut, do you dare tell me what to do?"

A chill of fear and excitement ran through her. "No, Sir! I'm sorry."

Janice shook her head. "You see what I mean? What the fuck? Seriously!"

Joy agreed. "I didn't ever think I'd hear her say 'sorry' to anyone about anything. Ever!"

Heather's humiliation deepened even further, but that just stoked the fires of her raging lust. That's because I only have one Sir. The rest of you can go to Hell!

Alan looked down at his erection, now bobbing right in front of Heather's face. "Please come here, Aims. I'm having a hard time holding myself and doing everything else. Start stroking Alan Junior, okay?"

"M'kay!" His official girlfriend hopped up and began slipping and sliding one hand all over his already very wet pole. Amy seemed very anally minded these days, so she used her other one to poke a finger in and out of his asshole, massaging his prostate.

She stroked him just inches away from the top of Heather's nose, which was exactly how Alan wanted it to be. He knew this would torture Heather even more, and since he'd climaxed a few minutes before, he wasn't in any hurry to get orgasmic relief for himself.

Just the smell of his thick dick was intoxicating Heather's senses, and once again she let loose with an involuntary lusty groan. She stuck her tongue out in hopes of reaching his cockhead, smeared with pre-cum, but Amy cleverly left it an inch or so out of range.

Heather could feel her mouth watering in anticipation of being allowed to suckle on it. If asked, she still would claim to vehemently hate cocksucking, but somehow with Alan it was completely different.

Alan watched Heather's mounting arousal with amusement. He waved his hard-on around a little bit while Amy continued to hold it. "Yep, it definitely helps to have one of these. Bitchslut, I'll bet you won't mind having Alan Junior give you some attention, would you?"

Heather didn't even look up because her eyes were locked onto his tantalizingly close boner. "No, Sir. Not at all, Sir."

"Where would you like him to go?"

"Up my ass! Naturally, Sir. It's looking pretty good for my mouth right about now, Sir, but anywhere is good. Tits, ass, cunt, or ass. Did I mention the ass?" She snickered a little at that. "As you point out, my body is here just to please you. So I'll take it wherever you want to give it to me, and then I'll beg for more. On my knees. I'm your bitchslut, Sir."

She was amazed at how excited and happy she was to be saying these things. She almost forget the depressing fact that the others were there, and yet she didn't, and that fact raised her arousal much more than she realized.

"Interesting." Alan stepped forward, bringing his erection close enough to actually hit Heather on the nose.

She tried to lick it, but it was a fraction of an inch too high. By the time she adjusted to the right height, it was out of range again.

She was extremely frustrated, to say the least. She let out a long noise that was between a lusty moan and an annoyed whine. Gaawwwd! I want that cock so bad! But he's going to make me work for it, isn't he? He's so cruel!

He asked her, "What about the cheerleaders?"

"What about them?" she barked impatiently, as she still tried to lick his shaft, in vain. She hated being reminded of their presence, even as the humiliation kept her horny.

"Seeing as you're my personal cum dump, don't you think you were treating them badly, before I came in? Don't they deserve an apology?"

She growled. "Sir, why do you always have to push... GRRR!" But then she calmed herself by taking a couple of deep breaths. "Um, girls, I'm sorry for being bitchy. There! Sir, can I suck you already? Please! I'll be so good to it, I promise!"

He figured that even he had to know when to not push his luck. So he said, "Kim, please come here and lend a hand or two if you like."

Kim was up instantly. She put one hand on Alan's stiff dick to share it with Amy, and brought the other to his balls.

Heather's eyes went wider and wider as she saw three hands frantically fondling Alan's privates mere inches from her nose. She glimpsed Amy's arm between his legs, indicating where the fourth hand was doing its work. She tried to lurch forward and touch the tip of his penis with her tongue, and she just managed to reach it, some of the time, depending on what the other hands were doing to it. But the slight touches only increased her desire instead of satisfying it.

She thought, This is seriously humiliating. I feel like some kind of stupid mule with a carrot dangling just out of reach so the mule will keep moving, but I can't help myself. Oh God, it tastes so good! Just the little touches and tastes I get are divine! I think I'm losing my mind! If he doesn't flood at least one of my holes with that heavenly nectar, then ... well, I don't know what! I need it!