6 Times a Day

Iveyflame Special ?? [ 15 / 15 ] 5K words

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Thinking, I guess I AM a prick, he finally began to slowly thrust in and out of her with the kind of deep strokes that Heather wanted so badly. One good result from the last minute or so of his teasing was that it had allowed her ass to loosen up a little bit more. That meant the fucking was extremely pleasurable for both of them, instead of being a frustrating struggle. It was somewhat like fucking an extremely tight, muscular, and very strong pussy. Any tighter and it would have been too painful, but this felt just great.

He was also quite surprised that he didn’t feel an overwhelming need to cum. He’d been on the brink from well before he started, but somehow, once he was deep in her ass, his urge to cum lessened quite a lot. He wondered if it had to do with the fact that she was so tight that it was almost painful. He decided not to worry about it too much, and just enjoy riding this seemingly endless erotic high.

With his steady thrusting, Alan quickly reduced Heather to a quivering mass of subservient Jell-O. He could tell she was loving it by the way she shrieked incoherently as his strokes started to move faster and bring both of them even more pleasure. That only caused his ego to swell even further. His bad side was definitely in full control now. He got a great kick out of yelling rude things to her as he plowed her butt from behind.

“Who’s a rude cunt bitch?” he growled as he slapped her left butt cheek gleefully.

“I am!” Heather gasped happily while getting rammed on a deep stroke.

“Who’s nothing more than a pussy life support system, good for nothing but being fucked?”

“I am!” A thin line of drool dripped from the corner of her mouth and then was flung away by all the rhythmic shaking of her entire body.

“Are you my personal cunt?”

“Yes!”

“Are you my cum dumpster?”

Heather didn’t even hesitate to answer. “Yes!” At that moment, at least, she was fiercely proud of it and willing to shout it to the whole world. She was well aware that Janice was listening, but she didn’t even care that much. She was that horny.

Alan straightened his back, withdrew his stiff rod out of her nearly completely, and then shoved it back in with all of his might. The pain was excruciating for him as his wide cockhead forced its way in past her still very tight sphincter muscles, but it hurt in a good way.

She clenched her teeth to keep from losing all control. Then she let out a piercing scream.

Janice, still watching intently, had to temporarily stop playing with herself so she could plug her ears.

“Who’s your daddy, you common whore?” he yelled.

“You are!” Heather mewled helplessly as she rocked under his onslaught. Her entire body was literally rocking on all fours.

He gripped her ass cheeks to stop her from rocking back and forth too much, especially since the rocking left his boner in the middle of a tug of war. “And who’s an arrogant bitch who needs to be put in her place?”

“I am!” Tingles of excitement shot up and down her spine.

“Hey, sperm breath! What’s your only purpose in life?”

Heather shouted out her answer so loud that it sounded almost as if she’d been split in two. “To fuck! And get fucked! By you!”

Alan loved her “by you” comment. Little additions like that showed she was really into it and not just parroting the bare minimum of what she thought he wanted her to say. His ego swelled even more.

And so it went. Not only did Heather not mind the names, she loved them. The worse he treated her, the more she loved it. She couldn’t figure out why, because with all her previous lovers she’d brooked no insults or sassy attitude at all.

She actually felt high from the whole experience, like she’d just taken some powerful and wonderful drug. She already realized that she would have to have her ass filled regularly from now on, and that only Alan was man enough for the job of keeping her butt properly and thoroughly fucked the way she wanted and needed it.

Neither Alan nor Heather realized it just yet, but Heather happened to be one of the small minority of women with an overabundance of pleasure receptors in the ass that enabled her to absolutely love anal penetration from a purely physical point of view. The fact that she considered it naughty, depraved, and deviant made her love doing it even more. That her mother had expressly forbidden her from doing it was like the icing on the cake.

He mercilessly fucked Heather while she crouched on all fours. He didn’t care about the limited time left, or Janice, or the fact he was actually in school, or anything else but his fucking task.

At least, he forgot about those things most of the time. But as time passed, he heard Janice huffing and puffing increasingly loudly, even louder that Heather’s constant desperate, sexy moans. Right at the same time, Heather came hard, and flopped to the floor. He suddenly picked her up and carried her limp body about five feet to a spot right in front of where Janice was seated masturbating. He hoped this sight would help Janice have an especially great climax. He forced Heather’s big, tanned tits down onto the cold floor. With every thrust, he pushed her whole body into the hard ground.

But Heather seemed to actually prefer the rough treatment. Feeling her erect nipples rub on the cold hard floor aroused her even more. Knowing Janice was staring down at her from only a few feet away somehow turned her on still more. Heather’s screams were of a woman at the absolute peak of ecstasy. She didn’t even know if she was having an orgasm at any given moment or how many she was having overall. It seemed to her as if every single second Alan thrust in and out of her ass was yet another great orgasm.

Alan briefly looked at Janice as he repositioned himself. Her naked body was so close, he felt like he could reach out and touch her knee.

Janice appeared both terribly aroused and yet a bit afraid. She seemed to think that she would be getting the “Heather treatment” next. She had no desire to be bullied and insulted by Alan like that. But on the other hand, she longed for the ecstasy that Heather was obviously feeling. And the way Alan had put Heather in her place really turned Janice on. She was busy frigging herself to an orgasm, and it was far from her first; one could easily tell by how wet her hands and thighs were.

Alan was finally ready to cum, but he knew that if he did that he’d have nothing left for Janice. So he waited until Heather had a particularly intense series of rippling convulsions. It felt like her strong asshole was trying to pulp his dick. He guessed that meant she was having another orgasm, though it was hard to tell for sure. For a second or two he was certain the erotic pressure had pushed him past the point of no return and that his cum would shoot out of him, but a fervent squeezing of his PC muscle just managed to save the day.

Then he suddenly pulled out, and he took his hands off Heather altogether. He looked down and saw her well-fucked and hungrily pulsating asshole gaping back at him, still molded to the shape of his rigid penis. A thin film of sweat and her pussy juice covered her crotch and sparkled in the fluorescent lights overhead. Her ass cheeks had big red marks from where he’d slammed or clawed at her.

“Hey, what are you doing?” moaned an annoyed Heather. She shoved her ass backwards as if her anus could find his dick and gobble it back inside.

“Patience, Heather, patience. Who here has the cock?”

“You do,” she answered glumly.

“And who’s in charge here, slut?” At first she didn’t answer, but he poked and rubbed his boner against her ass. The tip slithered in the space between her pussy and anus, but failed to enter either.

“You are.” Saying that really rankled her, but at this point there was no way to deny the obvious. Besides, she knew it was an established “fact” already, based on what had been said before.

“Damn straight,” he said as he stood up on shaky legs and took his soaked erection far from her crotch. He desperately needed to cum, but he wasn’t going to do it in Heather. Not only did he still have Janice waiting, but he thought about how the aloof, arrogant Heather had cockteased countless boys at the high school and felt a sense of satisfaction to be giving her a taste of her own medicine.

“No! Wait!” cried Heather. She still felt boneless from her climaxes, so she made no attempt to get up or even move. But she said very emotionally, “You’re gonna leave me unsatisfied. Please don’t go!”

“Oh come on. You came lots of times. I could tell.”

“Yeah, but you haven’t cum in my ass! I’m gonna have the mother of all orgasms when you cum in me there, I just know it!”

He was cocky. “Hmmm. You seem to be right about that. But I only promised you a consolation prize. Janice gets the main reward.” He had no choice but to leave her like that. There was no way he could do them both right then.

Heather looked upset, but in fact she wasn’t that upset. She’d been fucked to oblivion and she was feeling the friction burn from insufficient lubrication already. Her ass really couldn’t take much more right now, even if her libido had wanted to keep going. She had yet to learn how good it could feel to have a big load of hot cum erupt inside her, flooding the steaming hot depths of her ass, so she didn’t know what she was missing.

With every passing second though, she felt the fight going out of her. She slumped to the floor and just panted heavily. It was all she could do to resist the urge to pass out.

Alan could see he wasn’t going to get any more grief from Heather for a while. He turned to Janice.

She sat in her chair with her fingers still in her crotch. She looked up at him with trepidation. “You’re not going to be like that with me, are you?”

He laughed. Then he realized he must look like a wild-eyed, overexcited, arrogant, sex maniac. He was still riding erotic and egoistical highs, but he forced himself to calm down some and speak in kind tones. “Don’t worry. Not unless you want that kind of treatment.”

“No thanks!” She was so distraught by that idea that she stopped playing with herself.

“I thought not. I only fuck like that with Heather. It’s kind of a special thing I’ve got going with her. I’ll be as nice with you as you want me to be.”

Janice muttered, “Thank God.” She was beside herself with delight and relief, both to hear that and to know that she had a good fucking to look forward to. She was even happier to see Heather was still awake and slowly recovering. It would make the sex all the sweeter if her enemy was forced to watch her get what she’d been denied.

Alan remembered Suzanne’s advice that one should never go from fucking an asshole to a pussy. He took his condom off and walked to the back of the stage where there was a sink. He used his hands to splash water all over his groin, and then he washed himself thoroughly with soap. When he was all cleaned up, he got a new condom from his discarded clothes and put it on.

He was too tired to talk while doing all this. Heather and Janice refrained from talking too.

Heather had recovered some more and was able to sit up. She was still completely silent though. She was trying to digest what had just happened. She instinctively knew that this was a pivotal event in her life, because she’d enjoyed the anal sex so much. She felt like someone who had just shot heroin for the first time and knew in that instant that they would be a heroin junkie for the rest of their life.

Anal sex felt so great that she knew it was something she absolutely had to have from that point forward. She also felt instinctively that she had to have it specifically from Alan. He knew exactly how to push all her buttons. Even if she could find some other guy willing to do it – a big if – she knew it would pale in comparison. She couldn’t admit it consciously, but the name calling and being forced to beg and wait was a big part of why she had loved the experience so much.

But now she had a problem. She needed Alan like she needed food to eat, but she was determined not to let him know that. She couldn’t stand not being in complete control. He already had a strangely powerful grip on her, and she didn’t want that to get any worse. She thought, He’s a NERD! I keep forgetting, but he’s just a nerd! Phew, that’s a reassuring thought. But… damn! How could a mere nerd rock my world like that?!

Alan, meanwhile, was thinking about Heather as he admired her sweaty, disheveled, and exhausted naked body. She’s a bitch in more ways than one. I just want to treat her like a bitch; like an animal. I want to slap her around and spank her. But that’s not right! What am I saying?! Even Heather has a heart and has feelings. If I can train her and bring her to heel… Damn! A dog metaphor again.

A malicious mood filled his head like a thick fog. He sat still for some long moments until the fog lifted a little bit. I have to get a hold of myself! But my point is, if I can fuck the evil out of her and correct her arrogant ways, there might be a nice person inside, waiting to come out. I’m gonna fuck Janice nicely now, and show Heather that she can be fucked nice and gentle when she deserves it.

Little did he realize, but the last way that Heather wanted to be fucked by him was nice and gentle.

He walked to the couch where Janice was sitting. “Finally. I’m all set now. Sorry to keep you waiting so long. But hopefully you found the show somewhat entertaining.” He sat next to her and caressed her arms and cheek.

Janice relaxed further as she realized he really wasn’t going to treat her like he’d treated Heather, even though his eyes still looked a little bit crazy. She replied as she ran her hands across his chest, “Definitely. It’s funny, but I don’t hate Heather so much anymore now that I see how she’s so pathetically desperate for your cock.”

Heather had been about to complain very vocally that Alan needed to finish what he started, but if she did that now it would only confirm what Janice had just said. Instead, she flailed around for a comeback. “Who’s pathetically desperate? Looks like you are, Janice.”

Janice laughed derisively. “Yeah. Right. Like I would EVER willingly call myself a ‘cum dumpster.'” She mimicked Alan’s voice, “‘Who’s nothing more than a pussy life support system, good for nothing but being fucked?'” Then she mimicked Heather’s gaspingly horny reply in a mocking tone, “‘I am!'”

Heather instantly blushed and was furious. She realized she had a massive problem on her hands. Her enemy Janice had heard her say the most humiliating things imaginable. She instinctively trusted that Alan wouldn’t repeat them anywhere, even though they’d never discussed it. She knew he was prudent and smart, and that was the prudent and smart thing to do, if he wanted to fuck her again. But she knew just as certainly that Janice could have the entire school talking about Heather’s shame within an hour. Of course some people might think Janice was just making it up, but there would be sincerity in Janice’s tone and an unavoidable embarrassment in Heather’s denials that would fan the gossip flames.

She rushed over to Janice and stared into Janice’s eyes from inches away. “Listen to me and listen to me good. If you breathe ONE WORD about what happened in here to ANYONE, I will KILL YOU. KILL YOU! You’re dead! Do you understand me?!”

Janice shrank backwards in terror. “Kill me?!”

“Not literally, you fool, but I will make you WISH you were dead. Not only that, but I can tell how lovey-dovey you are for Joy. You can deny it till you’re blue in the face, but I can see how you look at her with googly eyes. Before I utterly crush your will to live, I’ll first turn on Joy and ruin her. If I hear ONE WORD about the things Alan called me here today, Joy will be expelled and in prison within a week. And that’s just for starters!”

Janice had quite pale skin to begin with, but she was completely white with fear now. “You wouldn’t!” Notably, she didn’t deny that she was in love with Joy.

“I would. And I can. Don’t test me!”

Alan also blanched. For the first time, he began to realize just how powerful and vindictive Heather could be. He had no idea how Heather could frame Joy and put her in prison, but looking at the determination and hatred on her face, there was no way to deny that she could do it.

But he also realized that the one thing he had going with Heather was an impression of superiority and invulnerability. If she sensed any weakness from him, he was finished. Thinking, In for a penny, in for a pound, he started speaking without knowing what he was going to say. “Listen. Hey, you two, listen to me.”

Heather and Janice turned in his direction. Heather still clutched Janice’s hair and her face was twisted with hate, but Alan sat there practically in Janice’s lap.

Alan continued, stalling for time, “Hey. No fighting. What am I – a bump on a log? I’m here too, you know. I’m not going to allow you to fight. Janice, don’t worry, I won’t allow Heather to do that to you or to Joy.”

Heather now turned her anger at him. “Oh yeah? Says who? Don’t even THINK-”

“HEY! Hey! Hey! Hey! HEY!” Alan shouted over Heather until she let him speak. “Listen! Heather, I won’t allow your secrets out of this room. Don’t worry! Like I said earlier, what happened here stays here. I certainly am not going to tell a soul. I don’t kiss and tell. It’s not my way.”

That calmed Heather down a lot. It confirmed her instincts that he could be trusted. She turned her angry face back at Janice.

But Alan kept talking. “Janice, I’ll try to stop Heather from doing anything crazy. It’s pretty obvious that she loves anal sex. If she retaliates on you, she won’t be getting any more sex from me. Period. But on the other hand, if I were you, I wouldn’t even think about crossing her on this. She obviously has a lot of ways of getting even. It’s better for all three of us if we just stay quiet about this. Janice, may I also remind you that if you go blabbing to everyone about Heather, then I can’t trust you either. There’s no way I’m going to have sex with you now or ever again if you can’t be discreet.” 𝙚𝙙𝙣𝒐𝙫𝙚𝙡.𝙤𝙧𝒈

Janice looked back and forth between Alan and Heather. Alan looked sincere and determined while Heather just looked plain evil. After a long pause, she said, “Fine. Who said I was going to say anything, anyway? I’m not.”

Heather pointed right in Janice’s face. “Not even to Joy!”

“Fine. Not even to her. But you and I aren’t done, Heather. Now I know how you REALLY are. You’re the most pathetic girl I’ve ever seen. I’ll never be able to look at you in the same way again. You bring disgrace to the entire female gender. ‘Oh! Alan! Please let me be your cum dumpster! Please?!'”

Alan immediately spoke up before Heather could go ballistic. “Listen! Janice, being quiet means not mentioning these kinds of comments in the future to me OR to Heather. Really, you shouldn’t have been here. That was a mistake. But you were. The things Heather and I say to each other are just between her and me. If I say something sexual to you, then I expect the same discretion from Heather. I know you two hate each other, but I don’t want to get caught in the middle of your little feud. If that’s how it’s going to be, I’m going to wash my hands of both of you, and good riddance.”

Heather and Janice both shouted at once, “NO!”

Heather could hardly wait to get fucked by Alan again, especially in the ass. In fact, she was surprised to find her own hands wandering back to defensively clutch and massage her own ass cheeks, as if to soothe and reassure her rear end that Alan would soon be back for more.

Janice, meanwhile, had just seen that Heather had been overwhelmed by a revelatory sexual experience and she wanted something similar (though not in the ass). If what Heather had was the “consolation prize” then she could hardly imagine what the first prize would be like.

He said, “So, if either of you want to take part in more erotic adventures like this, the most basic thing is that nobody talks. Can both of you be mature and cool enough to do that?”

Both girls nodded, rather sheepishly.

Alan was pleased that he seemed to have some control of the situation. The truth was, if Janice did spread word of what had happened to the gossip networks, it would not only devastate Heather but also seriously complicate his own life. Calling Heather a “cum dumpster” would hardly endear him to anyone, especially the female half of the school. He could already imagine Christine hitting him with a barrage of withering insults, if not her open hand. Worse, his best friend Sean was so moony over Heather that Sean would hate him. In fact, if Sean merely found out that he’d had sex with Heather, Sean would probably be devastated.

He turned to Heather. “I think it’s best if you go. NOW! Janice is NOT going to talk; I’ll make sure of that. Calm down and take a chill pill. There’s no problem here. One of these days I’ll finish what I started with you here today, and cum in your ass.”

Heather could see the wisdom of leaving. She realized that she was way too upset to think clearly and she didn’t want to say anything in the heat of the moment that could ruin her chances with Alan. She got up and went to wash up and put her clothes back on.

But still she stewed. “‘One of these days?’ What does that mean? Alan, you can’t leave me hanging like this! I really want you to cum in my ass. It somehow feels incomplete if you don’t.” She was going to plead some more, but then she remembered Janice’s comment about being “pathetically desperate” and that shut her up.

“Heather, we’ll talk later. Don’t worry; everything’s good. That was fun. I definitely want to cram your butt again – you have a really tight ass.” He ran a hand over her nearest ass cheek. At first he just fondled her over her skirt, but then he slipped a hand inside her skirt and panties and gave her ass flesh a good squeeze.

Heather was somewhat mollified by his words. His promise was something she could work with and build on, as she hopefully molded him into her anal-sex boy toy. She was already scheming on how to find a way to get her newly-discovered anal-sex fix from him every day. She continued to clean up and dress while Alan and Janice waited silently for her to finish and leave.

Alan’s penis had gone flaccid during Heather’s big angry outburst. But halfway through her getting dressed, Janice knelt down in front of him and started bobbing on his erection, obviously trying to bring him back to full hardness.

Heather had already put her panties and skirt back on, but she pulled her panties right back off again while keeping the skirt (because she’d deduced correctly that Alan enjoyed the cheerleader look). Knowing that he was watching her, she slowly put her tennis shoes on, a process that provided a reason for her to do a lot of bending over with plenty of ass wiggling. Then she turned around to face him.

It was her intention to perform a semi-naked dance for him, but when it actually came time to deliver she realized that she just didn’t have the energy. She was literally all fucked out. So she just did a mellow striptease of sorts, pulling her cheerleader skirt down in a sexy manner, before pulling it slightly back up again. Doing this gave her confidence. God, I have such a fucking hot body! I really am the most beautiful girl in this school, by far! Not even Christine looks THIS scorching! A total nobody like Alan should count his lucky stars that I deign to spend any time with him at all.

She pulled her skirt just below her pussy. Hey, stud, you want this? You wanna tap this sweet pussy? You wanna drill me with that big fuckin’ cock of yours?

She pulled her skirt back up, but then turned around and pulled it just below her ass cheeks once again. Or do you wanna take me like this? Are you gonna make me bark like a dog when you take me doggy-style, you motherfuckin’ beast? She smirked, smiling as she considered the possibilities.

Then, facing him again, she said, “Alan, don’t worry. I’m definitely cool and mature enough to understand the need for total discretion. I know how to give you a good time, and you know how to give me a good time. Together we can have a very good time together.”

When she was done, she turned yet again and bent over. She made sure her skirt rode up enough to expose all of her bare and very tanned ass cheeks.

Alan just nodded in agreement. Janice’s busy lips and tongue had his dick fully hard again, so he was somewhat preoccupied.

Heather considered saying more but realized that doing so would just prolong Janice’s blowjob and Alan’s enjoyment of Janice, and that bugged her. So instead she just straightened up and nodded in return. But even then she wasn’t quite done teasing, as she took her sexy time putting her panties and bra back on.

Finally, when she was fully dressed, she went to the door to let herself out. She ignored Janice, but didn’t know what to say to Alan. She suddenly felt strange feelings of affection for him, even as her asshole throbbed with a dull burning soreness from his recent violation back there. To her complete amazement, she sincerely found herself wanting to say intimate things or blow him a kiss in a very girly way. But she didn’t, primarily because Janice was there. In the end she just waved awkwardly and left.

She had a very funny gait as she walked away.