6 Times a Day



ReaperCrew [ 2 / 12 ] 3.5K words

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Suddenly Alan's sense of victory was overwhelmed by concern for Amy. He could feel her anus trying to "bite off" the head of his cock, which he already had inside her, which was an exciting mixture of pleasure and pain. "Aims, does it hurt?"

"Ye-hes..." came the muffled response. Her body twitched in time to the pulses of her anal spasms.

"Do you ... do you want me to, you know ... take it out?"

She turned her head until she could look at the concerned face of her lover.

He could see that her eyes were watering as she bravely tried to hold off tears.

"No, don't take it out. I want it. I want it more than anything. Just- just hold still while I ... while I get used to it." Her asshole throbbed and pulsed, powerfully. Her whole body shivered. "Good God, when did you get so gianormously humongerous? How much have you got in me? Half? More?"

He felt a little sheepish, answering truthfully, "You've um, only got the head so far, so there's uh ... still more where that came from."

She wriggled her hips ever so slightly, which made her gasp and arch her back again, lifting her head up off the bed. She then settled back down with one of the sexiest groans he had ever heard in his entire life.

He cautiously waited a little bit before he filled his hands with her big butt cheeks and started squeezing and kneading them with his fingers while gently rolling them around in his palms.

As if putting his hands on her ass flipped a switch, he felt her suddenly relax.

The tension drained out of her legs, and her breathing changed as she lolled her head to the side and sighed. Most importantly, her anus began to finally relax its "death grip" on him and seemed to decide that being stretched so extremely wide and penetrated by his cock wasn't really such a bad idea after all. Her asshole continued to pulse and throb just as it had done up until now, but did so more in welcome acceptance of his invading pole than in defensive and hostile rejection of it.

"Does it still hurt, Aims?" he asked, the loving concern obvious in his voice. He didn't stop playing with her ass cheeks, however.

It took her a few moments to answer. "Some, but not like it did at first ... and it's starting to feel really good now. Really, really good!" She paused, and then said in a slightly doubtful voice, "I'm ready for more."

To his astonishment, her ass slowly started to swallow up his erection, bit by bit, although there was still a fair amount of resistance to overcome. Like her anus, her rectum was just naturally smaller in size to begin with, and therefore naturally tighter than any he had ever experienced. As more of his erection entered her, the cockhead had to stretch the elastic walls of her rectum open wider than they had ever needed to be before.

She tried to keep her asshole relaxed, so as to make his penetration of her ass easier for both of them, but the virginal tightness of her interior was something she had no control over, especially since he was almost (but, fortunately, not quite) too big for her to accommodate without injury in the first place.

Although the area around the cockhead felt painfully violated as he fucked deeper and deeper into her virgin asshole, the feeling of the shaft behind the head massaging her tightly clasping rectal walls was unbearably exciting for her, to judge by the way her insides so actively responded to being fucked for the first time. She was very aware of every nuanced detail of his erection, from the shape of the veins within it to the heat and throbbing pulse of blood surging through it with his heartbeat, as she accepted more and more of his fuckmeat into her asshole.

She felt the delicate tickling brush of his pubic hairs against her butt and let out a great moan as his stiff pole sank into her yet further still. "YES! Almost there! ... YES! ... OH GOD! I'M SO FULL!"

He paused a few moments, and then resumed pressing forward. But as he did so he began to feel a new sensation. It felt as if she was tightening up inside, if that was possible, but lengthwise along his pole instead of around him as he would have expected. His cock had reached the end of her small rectum, and the last fraction of an inch he pressed into her stretched her tight and deep around his erection. It made him feel like he was pulling a tight fitting glove even tighter.

But then all movement stopped, and the yelling stopped too. She was overcome by the pain and struggled just to breathe. It was all she could do to remain there and take what felt like a gargantuan log shoved up a very tight channel.

He decided she needed another break to adjust, so with his cock still deep inside her, he cooed, "Great job, Aims. Great. I love you so much... Hey, you want me to tell you a story?"

She grunted her approval.

"Once upon a time, there was a beautiful princess. Her name was Amy and she lived in a magical kingdom. She was such a wonderful woman that I can't even begin to count the ways that she was special, but for instance, she had a great ever-present smile, awesome artistic skills, and a wonderfully creative way of abusing English grammar."

She was rapidly recovering, the pain slowly fading as her asshole adjusted to accommodate her lover. She giggled and mock-protested, "Hey!"

"What?" he asked said with false cluelessness. "I thought you'd find my story super-iffic."

That earned a happy snort and a laugh.

"Anyways, one day she met a nice prince, who sneaked up behind her and shoved an Inter-Continental Ballistic Missile up her ass. Then they lived happily ever after, although it was a bit difficult for her to sit most of the time, since he fucked her ass so much. The end."

She got a really good laugh out of that, and then commented, "That's just about what it feels like! ... But it feels good now. I'm starting to get used to it and even enjoying it. Why don't you start wiggling your ICBM around? Let's do it!"

He lovingly brushed her cheek and lips with his fingers. "Are you sure? We can wait longer so you'll adjust better."

She sighed, touched by his caring tenderness. She kissed his fingertips lightly, and then turned her head to look him in the eye as her asshole pulsed powerfully around his cock in anticipation of a good and thorough fucking. Her eyes suddenly looked a little wild. "Just do it! I want it! I want you! I want you to fuck me. Fuck MY ASS!"

He laughed. But after waiting only a little while longer, he started to slowly piston in and out. It seemed incredible how tightly his boner was being squeezed, but somehow it moved forward and back. He felt indescribably joyous and triumphant. He thought, This is the ultimate tight hole. If it were any tighter it wouldn't work, but this is just ... exquisite! It's like I'm drilling a hole in her with my dick. Wild!

Before long, Amy was vocally responding to her first assfuck, but in a totally unexpected way. Alan had expected Amy to scream the rafters off the house like she usually did when he fucked her pussy, but instead she was panting and gasping, moaning and groaning with the rhythm of their fucking. While he was glad that his ears weren't being pierced by her usual rattling shrieks, he was surprised by just how much quieter she was when he pumped her ass instead of her pussy.

"Aims, are you holding back on me? You're usually a lot louder."

"Nnnnoooo..." she groaned, as she pushed her hips back until her pussy kissed his balls. "I'm not hooooolding back on ... Mmmm. God that feels soooo gooood!" She wriggled her hips with his erection buried completely inside her. "It's just different. Feels different. Mmmm... This is how gooood you make me feel ... when you fuck my ah, ah, aaaahhh-hasssss! Yeeeessssss!"

He liked the way she sounded; her breathy moans somehow seemed even sexier than her loud shrieking. It reminded him that she was very much the daughter of the breathy, sultry Suzanne.

In and out he pistoned, in and out, over and over. At first he made a real effort to go slowly, but slowly and inexorably the pace sped up. Before long, he was cruising along at a very happy speed.

He thought, Not that long ago I could barely get my pinky in there. Now I'm sliding along, tight, but slick. So tight! So excellent! How is it possible? I LOVE this ass! He shoved himself in deep and whispered loudly to her, "Amy! I absolutely love your ass!"

She was beyond responding, except to grunt and groan even more emphatically. Her asshole pulsed and clutched at his deeply imbedded erection.

After a while, he remembered what a great response he got when he touched her clit, so he tried it again. This time, he didn't really notice a change, but then he realized she was probably climaxing as much as humanly possible even before he did that. Still, he kept playing with her pussy and clit while he continued to ride her rump.

Then, just when he thought she couldn't get any more excited, she did. Her whole body began vibrating, gently at first, but soon it was an intense shake. Her body shivered so convulsively that it felt like he had a human vibrator wrapped around his dick. She threw her head around like an overly excited go-go dancer in the middle of a dancing frenzy.

Alan, afraid that Amy might hurt herself, grabbed her wrists and pulled her arms behind her back to help restrain her thrashing.

The sight of Amy so obviously at the absolute peak of orgasmic joy made Alan extremely excited too. The sight of her thrashing her head around like the most reckless body slammer at the wildest punk rock concert was a sight to behold. It aroused him even more than the extremely pleasurable and tight tunnel he was vigorously plowing. He tried his hardest to stave off his climax, but he just couldn't do it, not with that image in front of him.

He bent forward and actually fell onto her back. He grabbed her body and held onto her like a drowning man clinging to a log in a raging sea. His balls tightened and churned, and then started pumping a veritable flood of cum into his sister's ass.

Then, to his surprise, as she started to cum too, he lost the ability to move his boner at all. His cock happened to be all the way inside when she squeezed him so tight that there was nothing he could do but freeze in that position. Each time another rope shot off deep into her ass, it was like an explosion of tight clenching and contractions that threatened to squeeze his cock clean off. That just made him feel even better, and shoot even more cum into her. In fact, the feeling of pain and pleasure mixed together from the tightness of her internal grip on him was absolutely fantastic.

When he was finally done, he just remained where he was, lying on top of her, still tightly clinging onto her. They remained like that for quite some time, simply recovering, while her active asshole kept throbbing and pulsing around his slowly deflating penis. Even these final throbs felt wonderful for them both.

He was in no hurry to talk, but after some minutes he heard the sound of her sobbing, and he had to ask, "Aims? Aims? What's wrong? Are you crying?"

"Yeah. But don't worry. It's tears of joy. I love you so much! Brother!"

He felt a surge of pride, but also chagrin. He thought, Uh-oh. This is what Mom or Brenda would call me taming a woman with my cock. Looks like Aims just got that much more tamed. She's going to be that much more sexually insatiable from now on. But fucking her in the ass is like double the feeling of anyone else's ass. Triple! Again, how can I take this much pleasure? It just feels too good! I could get seriously addicted to this ass.

He asked, "Can I ask you a question?"

"Sure, Brother. Anything for you." She still made tiny sobs, but they were lessening.

"I'm real curious. What's the second point you wanted to discuss?"

"Oh. That." She rolled over so she could look him right in the eyes, causing his deflating penis to slip from her aching hole. Her eyes were red, and there were tears, but there was a big smile, too. She remained in his tight embrace all the while. "I don't want to be all demand-y, but I do have another demand. The thing is, I wanted to see if I enjoyed anal sex first."

"And the verdict is?"

She giggled. "Duuuuuh! How can you ask me that? It was incredi-fantabu-wonder-tastic!"

He stifled a laugh, and then deadpanned, "Okay, just checking. I was worried you might think it was merely marvelo-stounding-tabulous."

She laughed really hard at that, and he did too. "Alan! I love you! You're so funny. You're too great!" She kissed him hard on the lips.

This led to some very prolonged and passionate tongue dueling. As much as Alan loved Amy before, he found his feelings for her surging to an all time high.

He broke the kiss after a while because he wanted to praise her to the heavens. But then he remembered the others might be watching and listening. He correctly suspected that Katherine had been watching before she'd gotten the dildo for him. He worried how she'd take this great anal sex experience with Amy that made her anal sex with him pale in comparison.

That put a big damper on his enthusiasm. I don't know about this camera system. Everything gets recorded? That's like living in a fishbowl. I think I'm going to keep it turned off in my room most of the time. I need my space! I have to be so careful about what I say and do, and that kills my spontaneity.

He refocused his attention on Amy and looked deeply into her hazel eyes. "I just want you to know that I love you."

"I know! You just said that, you big silly! But I love you too, so very much! You know what some of the others say about how we need to keep your thingy hard and pleasured at all times? It's SOOO true! God, that's all I want to do, is just give back the pleasure. But it would take a thousand blowjobs to equal how good you made me feel with that one assfuck. Maybe I'd better get started, once we wash up."

"No fair. Your mother is waiting. We really shouldn't do any more right now, but we'll be at it again soon enough. So what was this second demand of yours?"

"Oh yeah. Only that you fuck me up the ass, like, A WHOLE LOT! I had a feeling I was going to love it, because Brenda and I were talking about it and we were really getting into it, and now that I've had it, it's even better than all the anticipation! I think my ass is really sensitive."

"No kidding," he joshed.

"I think Brenda's is too."

He goggled at that thought. Brenda? She leaks gallons of pussy juice and yells loud enough to wake whole towns all the way to Arizona if I so much as tweak her nipple. It's frightening to think what would happen if I fucked her ass like that and her ass is as sensitive as Amy's! I would need to fuck her outside, and on the roof, to make sure I didn't drown in her torrential flood of pussy juice!

Another thought popped into his head while he nuzzled Amy cheek to cheek. "Aims? We'll be doing this a lot more, I'm sure."

He thought, That's true, but that isn't going to make Katherine happy one bit. But at least this may get me out of the two Katherine fucks for every one Amy fuck promise I've made. If I limit that to just vaginal sex, I'll still keep my promise and fuck both of them roughly about the same number of times per week. That's only fair, since they're both my sisters now.

He said, "But I have one favor to ask. Could you put off your sex with Aunt Suzy? I know that was planned for tonight, and I was looking forward to a good show as you two went all the way for the first time. But what we did was so draining. Plus, I have a feeling that after Aunt Suzy is done with me, there won't be any of me left. And I do want to enjoy watching that to the fullest."

"Oh, sure," she answered brightly. "We'd figured that out already, and pushed it off again to whenever you're ready. Mother said something about how she was going to drain your balls completely dry and turn your knees to Jell-O so you'd be unable to stand. So yeah, she thought you wouldn't be up for watching it, and neither did I. This mother-daughter tag team is gonna fuck you silly!" She grinned like the Cheshire Cat, beaming with pride and happiness.

"Oh, she said all that, did she? We'll just have to see about that. I think she's gonna be the one who won't be able to walk out of here."

"I can believe that" she agreed. "In fact, I'm just gonna have to stay here and cuddle with you some more though, because I'm Jell-O all over. I feel like boneless chicken!"

He smiled. He was proud that he'd overcome the challenge of her tight hole and made her so happy.