6 Times a Day

Iveyflame Special 🔥 [ 13 / 15 ]

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Alan finally walked back behind Heather and lewdly wagged his engorged dick at her ass. She couldn't see what he was doing, but he made sure to brush his boner against her firm bare butt. "Pull your cheeks apart nice and wide, you little cum-guzzling slut!"

Heather was growing increasingly excited by the prospect of finally having anal sex. When her mother Helen had sat her down to give her the "birds and bees" talk years ago, anal sex was the one and only sexual act that her mother had specifically forbidden. Helen had spoken of it in hushed tones of distaste and revulsion, as if it was one step shy of murdering someone.

Heather had been deeply intrigued by thoughts of doing it ever since. Her contrary attitude reveled in the opportunity to defy her mother's wishes. Yet at the same time, much of her mother's attitude had sunk in. Only in recent months had she finally dared to consider that act, trying some limited anal dildo play with Simone and hinting to some of her male lovers that she wanted to try out anal. It remained the ultimate irresistible sexual taboo for her.

Alan was also getting psyched up. He thought to himself, You know, there's something especially satisfying about fucking Heather's butt. Not only is she generally acknowledged as the most beautiful girl in school - although I personally think that Christine, Aims and Sis are all more beautiful - but just the idea of fucking her in the ass gives me the feeling of taking this far-too-bitchy and arrogant slut down a notch. In addition, our jousting matches are doing wonders at building up my confidence and aggressiveness.

He began rubbing his erection all over her pussy lips and also up and down her ass crack. In so doing, he used his hard-on like an artist's paintbrush to lubricate her asshole somewhat with her pussy juices. The tickling feeling of rubbing his bare cock through the valley between her quivering buttocks was also intensely erotic for him, and even more so for her.

However, he realized that probably wasn't enough lubrication. Luckily, he had an "ace in the hole" he'd refrained from revealing unless he needed to, and now seemed like the time. So he said, "You know, when it comes to anal sex, one can't use too much lube. And it's good to use a condom too. It so happens that I have both a small tube of lube and a condom in my pockets. Janice, would you please get those for me?"

Janice immediately went to where his pants had been tossed aside. "Sure thing."

But Heather complained, "Hold on. I don't mind the extra lubrication, 'cos I don't want that big dick of yours tearing up my insides back there. But a condom? That's bullshit! I wanna feel you cum in my ass! That's a big part of the experience!"

He replied, "In the future, we can try that out. But did you have an enema in the last hour or so? Are you completely sure that you're totally cleaned out in there?"

There was a long pause. Obviously, Heather was trying to figure out what to say so he wouldn't wear a condom. But finally she just huffed, "Fine. Whatever. Get on with it already, then!"

Since Heather wasn't resisting about that, he looked to Janice and said, "Could you please do me another favor and help with the condom and the lube?"

"With pleasure!" Janice immediately knelt down and stuck her head between Alan's body and Heather's ass. Although she had just handed him the lube and condom, she did not retrieve them. Instead, she started stroking and licking her way all over Alan's stiff erection.

Heather could feel Janice's hair brushing against her ass at different angles. She heard slurping sounds and soon contented feminine moaning sounds. She barked, "What the fuck is going on back there? I'm dying! Janice, if you're fucking around and wasting time, I swear-"

Alan interrupted, "Janice, you probably should speed things up. We don't have all day."

"Darn." She retrieved the condom and lube from his hand and started preparing his dick. She said, "Since YOU asked me so NICELY, then of course." Stated that way, it was an obvious rebuke of Heather and her rude behavior.

More long moments passed. Heather wiggled her ass impatiently. "Come ON, people! Jesus Christ. What is taking so fucking long?!"

Janice replied a bit snarkily, "I've got the condom on, and now I'm applying the lube and rubbing it in very carefully."

Heather exhaled loudly, in great frustration. "Yeah, I know what you're doing; you're jacking him off! God knows it's exciting to stroke his big, thick cock. If I were in your shoes, I'd take it in my hands and run my fingers up and down it, and breathe heavily on it, and bend over so I could..."

She realized with a start that she was getting carried away with her fantasy. "Wait a minute. Never mind that. Get on with it already, or heads are going to roll!"

Alan again sensed that Janice was pushing Heather too far, so he said, "Thanks a lot, Janice. That was great."

She reluctantly let go of his cock and sat back on her heels. "Any time."

Alan scooted up a few inches until his condom-covered dick was resting against Heather's ass crack. But instead of sticking it in, he rubbed it up and down her crack while also reaching under and fingering her pussy lips and clit.

Heather was practically delirious, mostly because she felt like she was on the verge of a great climax, due to the anticipation and build-up. The fact that he was fingering and teasing her like that made her worry that she'd cum so intensely that she'd be too wrecked to stay on all fours and get her ass fucked. She was trying her best to hold back from cumming, and the way he was fingering her was driving her crazy.

So Alan had to speed things up a bit. He began rubbing his cock around her anus more specifically.

She panted hard as she repeatedly thrust her ass back into his cock. She was literally trying to impale herself on it, but without success. His cockhead always seemed to be a fraction of an inch out of reach. "Stick it... stick it IN! God dammit! ... DO IT!"

He replied, "Not until you beg."

She complained, "I already did!"

"I know. And it was music to my ears. I want you to beg some more."

"Ha! Fat chance," she taunted.

Alan pushed his hard-on into her anus just a little bit, stretching it open ever so slightly, leading Heather to think that he'd given in. He knew that's what she'd expect from him since high school boys were not exactly renowned for their patience. But he kept his throbbing rod there and didn't go in any further. "Okay Janice, I told you this wouldn't take long. Get ready; it's your turn now."

Heather was so focused on getting Alan's dick in her ass that she'd completely forgotten Janice was there. The reminder caused her to explode in anger. "Janice, fuck off! What are you STILL doing here?! If you don't fucking clear out of this room this very instant, I will fucking DESTROY you! I'm not going to let Alan play you against me. Janice, do you hear me? Leave!"

Janice looked with worry to Alan.

Alan continued to toy around with pressing his dick into Heather's anus, but only a tiny little bit so as to give her a taste of what might be coming. He certainly wasn't anywhere close to pushing his bulbous cockhead past her angrily pulsating sphincter. "Heather, how rude. If I'm going to fuck your ass, first you're going to have to apologize to Janice. Then you're going to promise never to get revenge on her in any way. If you even try, you can forget this ever happening again. I have lots of other women to fuck, not just Janice. Heck, I could very easily go get someone else to replace her right now. So, first apologize, then beg. Beg me to fill your ass with my cock."

"You're mental! No way!"

He sighed as if he'd given up. "Sad. Your loss. Okay, Janice, I'm serious this time. It's your turn now." He pushed into and stretched open Heather's clenching anus so that his cockhead almost passed into her.

Heather assisted, pulsing her anal muscles and pushing her hips back to help draw him in, but he pulled away from her at the last second. Then he withdrew from her completely, placing his hard-on on top of her ass crack again. The sensation of the fine softness of her skin contrasted deliciously with the resistant firmness of the hard muscles of her ass, especially with her trembling under his touch in lustful anticipation of being impaled back there.

"Aaaargh!" Heather screamed. The loss of his dick was like a physical blow to her. She badly wanted to be fucked in the ass and knew that somehow Alan sensed this. I fucking HATE him! I can tell he's gonna keep torturing me until I do what he says. Why doesn't he think with his dick, like every other fucking boy his age?!

Her extreme need pushed all other considerations out of her mind. "Okay, fine," she said huffily. "Janice, I'm sorry. Forget the revenge over this, but if you dare cross me over anything else, your ass is grass. Alan, I'm begging you. For real this time. Now let's get on with this, shall we?"

Alan paused. He didn't like the way Heather was speaking. She'd said her words hurriedly and without sincere emotion, in much the same way a spoiled brat says the word "please" only because some adult forced them to do so. But he also figured that he could only push her so far. He was playing a dangerous game with her and could easily push his luck too far if he insisted on total surrender.

So he said, "That's better. That's not so hard, is it?" He began rubbing his erection up and down Heather's ass crack again.

Heather complained, "Fucking GET ON WITH IT already! Damn! You're so fucking aggravating."

"Okay, fine." Alan turned to Janice and winked at her. "Just one more sincere pleading should do it, my cute little cum dump."

"Arrgh! Alan, FUCK MY ASS! I'm begging you! I really am!" Her voice was angry, but there was no doubt she meant it.

Janice was looking on with great amusement. She was miffed at having to wait, and she didn't see how Alan would have time to fuck her too in what remained of the lunch period, but watching Heather get taken down a peg or two was almost worth it. Besides, she was having fun playing with her nipples and pussy.

Alan suddenly pushed his dick forward into Heather's ass, but the resistance was fierce. Now that he wanted to get his wide cockhead past her taut sphincter, he found he couldn't do it that easily. He tried pushing a couple of times while loudly grunting.

Heather tried to assist his attempts to penetrate her, opening her ass as wide as she could by pulling her ass cheeks apart with both hands. She grunted even louder than he did when she started pushing back in time with his thrusting to get into her.

But Alan's cock still wasn't going in. Her asshole simply wasn't dilating widely enough to permit him entry. He paused to rest for a minute, and said, "I've done this before and it wasn't nearly this tough. Heather, I think you're too stressed and tense. You need to relax your asshole before I can get in. But instead you're yelling at everyone and working yourself into a lather. That'll never work."

Heather was suffering. She knew that this might be her only chance to have anal sex while still in high school, since she had yet to find any other guy who was receptive to the idea. Besides, she was still right on the edge of an enormous climax, and desperately wanted the release. She complained derisively, "So what am I supposed to do, Einstein?"

He could feel how badly she wanted it. For one thing, the frustration and desire in her groaning was very obvious. "Quit struggling. You need to quit fighting and resisting me or we'll never get anywhere." He paused for dramatic effect, to make sure his next words sunk in. "You need to be sincere in your begging. That'll show that you've stopped resisting." His tone made it clear that he was being completely serious.

Heather's need had grown to such a fever pitch that she actually tried his suggestion. Arrgh! With the fucking begging again! Her pleading ended up sounding like a plaintive wail of desperation. "Alan. Please. Pleeease. Fuck me! Pleeeeeasse! Fuck me in the ass! God, I need it SO BAD! I'm begging you. PLEASE!"

"That's better," he said warmly as he smiled in triumph.

He tried pushing forward, but he still faced too much resistance. Heather had the most impressively firm and muscular ass he'd ever had the pleasure to touch, but the downside was that when those muscles were tensed up, they were like steel bars. So he said, "Now you've said it to me, think it to yourself. Think it, and mean it. You're my personal slut. My private cum dump. Your one and only goal is to pleasure my cock. Just... give in. Give in to the joy of serving my cock!"

He immediately wondered if he'd gone too far.

But Heather was so desperate to get assfucked that she was ready to try anything. She sincerely thought, Give in! Give in! Relax... I'm a good slut. Alan's slut. Nothing to fear. He's gonna fuck me, and I'm gonna love it! Give in... Serve his cock... Like a good slut...