6 Times a Day

Iveyflame Special ?? [ 14 / 15 ]

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Alan could sense her muscles relaxing. He suddenly grabbed her ass with both hands, spread her cheeks widely apart, and thrust strongly forward. He had been afraid of doing that before for fear of hurting her, but now he went for broke. To his great pleasure, his bulbous head pushed on through the powerful grip of her clenching anus. With surprising suddenness, he was in her.

Heather was ecstatic, but also in pain. She threw her head back and howled. “URGGHH! YES! Oh! Jesus! JEEESUS! Fuck, that hurt! … Finally! Fuck me, you prick! Fuck me hard! Give it to me!”

She came hard. However, she didn’t want to give him the satisfaction of knowing she’d cum already, so she did her best to hide it. She also managed to stay on all fours, even though it seemed for a while that her limbs had turned to Jell-o.

Alan was extremely pleased with himself, even though he wasn’t aware that she’d climaxed. He hadn’t really intended to make her beg so much, but it had worked out better than he’d expected. He also knew from talking to Suzanne about anal that it would be prudent to give Heather’s ass a chance to adjust to his large size before going in any deeper.

Besides, the crushingly strong grip she was exerting on his shaft meant that any additional penetration was, for the moment at least, quite impossible. So he figured it was a good chance to mess with her head some more, since he had to wait for her strong asshole to relax before she could take any more of him in any case.

“Heather, did you call me a prick? I guess I’ll have to pull out. And after all that effort, too. What a shame.” He sighed in disappointment and pulled back gently. It wasn’t enough to pop out of her, but it was enough to make her feel that he could.

“Alan, you are a prick!” She clamped down with her powerful anal muscles in an attempt to prevent his penis from escaping her ass.

He was surprised by her outburst. He thought he had her over a barrel at the moment, in a very literal sense.

She continued, “But I mean that as a compliment. Believe me, I’m a prick too, so I can recognize one when I see one. God, you’re so fucking evil, making me beg. But I love it! Don’t you have any kind of fear? Don’t you know what I could do to you?”

He gave that some thought. Frankly, I’m surprising myself too. Why DON’T I have more fear of her? Just last week I was too afraid to even talk to her, and now I’m acting like this… I guess it’s because I don’t really have much to be afraid about. What’s the worst she could do? She could make me a complete social outcast at school, but so what? I’m headed in that direction anyway. I’m losing all my friends to my sex mania.

But on the plus side, I have four wonderful, loving, and incredibly beautiful women at home. They’ve caused my confidence to double and then triple again just in these last few weeks alone. My entire school life could be a complete social disaster and who cares, ‘cos I’m just marking time until I can be home and playing with all those round tits and asses again anyway. Except for Glory, of course. She’s the shining bright spot in my school day.

And if Heather tries to destroy me, that’ll make Glory stand by me all the more. I’ve got so much amazing love and sex going on everywhere else that Heather’s worst doesn’t seem that bad. It’s possible she could get some football players to beat me up if she was really pissed, but that doesn’t seem her style. She’s all about psychological power. She wants to control your mind, not just your body.

But the bottom line is that she needs me too much. I haven’t had that much sex with her yet, but I can already tell that she needs me much more than I need her. So I can throw caution to the wind because her threats are mostly empty. Ha! This is fun!

He replied, “Heather, to be honest, I don’t care. The thing is, I’m fucking too many women who are more enjoyable in and out of bed than you’ll ever be. I’m fucking you mainly out of pity because your other male lovers appear to be such a pathetic bunch. You basically said so yourself.” ｂ𝚍ｎｏｖ𝚕．ｃｏｍ

That wasn’t true, that he was fucking her only out of pity. No one could deny that Heather was one of the most beautiful girls at the school, along with Amy, Katherine, Heather’s best friend Simone, Christine, Donna (a brunette social queen and Heather’s main rival), and maybe one or two others. Heather was also very sexually skilled and enthusiastic, thanks to her long-standing love of fucking, and Alan did greatly enjoy fucking her. Plus, he got a great kick out of mentally fucking with her. But he wasn’t about to admit any of that to her face, especially since she would take it as a sign of weakness.

One nice thing he discovered about having his dick in her ass was that she was so overwhelmed by the feeling of being stretched open and stuffed that she was slow on the uptake. He knew that if he gave her the chance, she’d soon be complaining about how she was the best and most beautiful girl in the school. So before she could recover her wits, he pressed deeper into her ass.

With one long and agonizingly slow thrust, he pushed his condom-covered shaft through Heather’s tightly stretched anus and deep into her spasming, rhythmically contracting rectum. He kept cramming more and more of his meaty pole between her quivering buttocks until, at last, he found himself buried balls-deep in her ass.

He let out a heavy sigh of relief and satisfaction.

While penetration had actually been reasonably quick for Alan, given that he was going where no one had gone before, for Heather it had seemed as if time had slowed to a crawl. Her whole world had contracted to just the sensation of being filled agonizingly slowly by the invading beefy monster that was sinking further into her butt.

There had been feelings of pain as his cockhead had stretched her wide while traveling deeper and deeper into her. Yet behind the head she felt a delicious friction from the shaft sliding through her tightly clenching anus and along her rectal walls. The way his erection pulsed and throbbed as he had continued to push it deeper had felt so good that she’d thought she was likely to pass out from the sheer pleasure of it.

As his rigid boner was penetrating her, she’d reached back and pulled her ass cheeks further apart, arching her back to slightly improve the angle of penetration.

All along, she’d kept telling herself, Okay, that’s all the cock he’s got to give. There can’t be any more than that! And yet, somehow, still more of his meaty thickness violated the as-yet-unfucked virgin depths of her ass. If, during that time, she’d been asked the length of Alan’s dick, she would have said it must have been at least fifteen inches long. She had even half-expected to feel a large bulge in her abdomen from the tip of his invasive log.

She’d whimpered and shivered as his thick cock had continued to plow through territory that had never before been reached, by anal dildos or anything else. By the time he’d finally bottomed out, she was on the verge of tears of both pain and joy. She’d kept her eyes tightly shut, and at the end she’d thought, I hope Janice isn’t looking! But of course she is, dammit! The fucking shame and humiliation. First he made me beg; now he’s splitting me in two! She must think I’m the ultimate slut, taking twenty inches of cock in my ass! Okay, maybe it’s not really twenty, but it sure as hell feels like it!

Alan had also been moved, but not by how deep he’d gone. Just like he’d felt during his first experience of anal sex, with Suzanne the day before, what really struck him was how tight Heather’s ass was. His cock was being squeezed all over in the most delightful way just by virtue of being inside her there. He could hardly conceive how good it would be when she learned to loosen up enough for him to thrust in and out without great difficulty.

He didn’t have much to compare the feeling with, since he’d only had anal sex once before, so he had no idea how unusually strong Heather’s ass was. But he did notice that the pressure she could exert on him was far greater than anything he’d experienced with Suzanne, and that was when Heather wasn’t really trying to crush his cock by flexing her muscles deep inside.

Heather, though, apparently didn’t realize that it was a good idea to wait a bit for her ass to adjust to his deeper penetration. She thought, I want more fucking and I want it NOW! His comments about fucking her out of pity were completely forgotten, at least for the moment. She squirmed and wiggled and goaded him on, saying, “Please, for the love of God, don’t stop! It’s just getting good! Push! Push it in and out!”

Alan still just rested his rigid erection all the way inside her and tried not to say anything. This was difficult to do because every time her asshole throbbed mightily around him, it felt like her anus was trying to bite off his dick and swallow it whole. Yet even though the intense pressure hurt some, it was also extremely pleasurable for him. It was an orgasmic struggle just to keep his cock in there and deal with her powerful clenching as she pulsed around him; so much so that thrusting almost seemed unnecessary.

Heather clearly didn’t feel the same, though. She continued, “Alan, I’m begging you! Fuck my ass! Fuck it good! I’m your dirty slutty anal whore and I NEED your cock! That’s right; I said I’m your dirty slutty anal whore! I love it! I neeeeed more! Please! Pleeeasse! I’m begging you!” As she said this, she reached around and tried to push him back while rocking her hips forward. She hoped to push him almost all the way out and then pull him back in.

But he could tell what she was trying to do. His firm hands on her ass cheeks kept her from gaining any leverage, and since she was on all fours there was nothing on the other side she could push against. He said with surprising calm, “Relax, Heather. Chill. This takes a couple of minutes. I can’t do it right if you don’t let your ass relax some more.”

She was still trying to thrust on her own, but to no avail. “Come on! Do it! DO IT! Don’t be a wuss. Fuck my ass already!”

“Hmmm. I don’t know,” he replied uncertainly after a long pause. “I don’t know if I like that attitude.”

Janice had been keeping quiet, hoping Heather would forget she was there. But she couldn’t resist saying, “Yeah, I don’t like that attitude either. She’s pretty demanding for a ‘dirty slutty anal whore.'” She snickered with glee.

Heather cursed, “Fuck you, Janice! Fuck off and DIE!” But she immediately turned her attention back to Alan. “Pleeeease! ALAN! For the love of God! Please! I’m not calling you a wuss; I’m just saying get on with it! What do you want me to say? You’re great! You’re the greatest. WhatEVER! Just fuck my AAAASSSSSS!”

Alan looked at Heather’s ass cheeks right in front of him. They were exceptionally muscular and firm. Heather couldn’t care less about her school homework, but she treated her body like a temple, eating right and working out religiously, and of course she had an incredible all-over tan. Acting on a whim, he raised his hand up and slapped Heather’s right ass cheek hard. “Bad Heather!” Then he did the same to her left ass cheek. “Bad Heather!”

She whimpered, “Please, Alan, please! I’m really begging you now. This is so real. Real begging! I’m your… I’m your slut! I am, and I mean it! Make your slut happy. Please do it!”

Alan was surprised at how little reaction she’d shown to those slaps. It seemed that getting fucked was the only thing that mattered, so even the ass-slapping was just a little-noticed distraction.

He turned to Janice, who still sat nearby watching and masturbating. Anal sex was something completely new to the feisty redhead. “What do you think, Janice? Should I do it?”

Heather groaned with frustration. She expected no sympathy from her nemesis. She listened closely, and was disturbed to hear the obviously sounds of Janice playing with her juicy pussy.

But to everyone’s surprise, Janice said, “Put the bitch out of her misery already. I can’t stand to see her beg. It’s pathetic.”

Alan was quite disappointed. He was having a lot of fun toying with Heather. Dang. I was gonna keep stringing Heather along. What the heck is wrong with me? It looks like even Janice thinks I’ve gone too far. Is this just an issue I have with the bitchy Heather, or am I slowly becoming truly nasty? I really should control myself. I shouldn’t call her hurtful names. It’s not right. But it’s so much fun to have this perfectly formed tanned cheerleader goddess whimpering and begging me to fuck her up the butt!

Even as he thought this, he pulled out a bit and then pushed in some. He felt an almost evil glee as he heard Heather moan and literally scream in a combination of satisfaction and frustration. She loved the little motion, but she wanted him to go all the way with deep penetrating thrusts.

She panted, “Alan, no! That’s the wrong way! I’m your anal slut! I’m your bitch! I’m your whore! I’m your slave! I’m your anything! Just put it in! No one has EVER fucked my ass before and I just HAVE to have it! Please!” She appeared to be on the verge of tears as her ass cheeks quaked and unsuccessfully tried to squeeze and suck his shaft further into her.

He thought, “I’m your slave”? Wow. I like the sound of that! She must really need it, especially to say that right in front of her enemy Janice. He snickered as he watched Heather’s perfectly tanned ass ripple and quake with the need for his penis. “Well, since you asked so nicely, my lovely blonde slut. Please IS the magic word.”