6 Times a Day

‘Someone’ Special [ 11 / 20 ] 3K words

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Alan and Amy returned just after midnight. Susan had already gone to bed after spending the evening at the party and having such a wild time fantasizing with Brenda. But Alan was a bit surprised to see that Katherine was just sitting around, waiting for them to return. His first thought was that she must be jealous. But in fact, it was just the opposite.

“Hey Amy,” Katherine said. “We all know that tonight is going to be your special night with Alan.”

Amy nodded excitedly.

“I’m very excited for you. Normally, I’d be a bit jealous…”

Listening, Alan thought, A bit?!

“…but you’re my best friend and I really am psyched for you! So let’s go get you prepared.”

“M’kay!” Amy gave Katherine a big hug.

Katherine gladly squeezed her back. Then she turned to Alan and said, “Brother, just be patient, and don’t go into your room until I say so, okay?”

Katherine whisked Amy off.

Alan sat around in the living room for about fifteen minutes, idly and impatiently channel surfing the TV. There was one part of him that didn’t mind waiting that much, because he was worried that his penis wouldn’t be up for the task (he’d been erect, briefly, at the party, but he wasn’t anymore). In fact, going to the party was mostly one big stalling tactic. He figured every minute could help.

“Hey Brother, she’s ready!” Katherine eventually yelled from the top of the stairs. “You can come up to your room.”

Alan walked upstairs, but saw no sign of Katherine. He guessed, correctly, that she’d deliberately made herself scarce so all the focus would be on Amy. Thanks, Sis! What a great sister. Hell, what a great family!

He continued to his bedroom and opened the door. To his great surprise, the lights were off but his sister had lit over a hundred candles, creating a very pleasant visual effect. As he walked in, he heard Marvin Gaye’s sexy “Let’s Get It On” album start to play on the stereo. The room was fragrantly scented. Most pleasing though was the sight of Amy sitting up in his bed.

“Hi Beau,” she said shyly, but proud of herself. She was covered with beautiful ribbons, held together by a number of big bows. One was over her boobs, another over her crotch, another in her hair, another keeping her hands tied, and the last one tied her ankles together. She pinned her arms behind her back, thrusting her ample globes forward to great effect.

“Wow. I’m blown away!” was all he could say. His fears of not getting it up went right out the window as his penis rapidly inflated.

He looked to his door, which he’d left often, and saw Katherine standing there. She knew she should make herself scarce, but was just too excited and curious, wanting to see his reaction with her own eyes. “Sis, you did this?”

“Yep,” Katherine said, smiling widely. “I figured our first time together was great, but it wasn’t at all romantic. I wanted Amy to have a more romantic setting.”

He was impressed with his sister. “What a nice thing to do. Aren’t you the coolest friend? And the best sister a brother could have!”

Amy blurted out, “Kat says that being all tied up like this symbolizes how, I’m like, totally yours! Isn’t that totally the greatest?”

“Yes, it is,” he replied calmly, but his dick lurched in excitement. He said to Katherine, “I know this is your linguistic terrain, but with all those bows, Amy really does look like a fuck toy. Like a sexy present, waiting under the Christmas tree to be unwrapped.”

Amy exclaimed, “Ooooh! God! That turns me on! Fuck me already!”

“Don’t just stand there,” Katherine excitedly encouraged her brother. “One of your fuck toys is eagerly waiting to be broken in. Undo bow number one, the hair bow.”

He undid the bow, which replaced the hair band that usually managed her long hair. ．

Amy’s hair immediately fell free in every direction. She shook it like a model in a shampoo commercial, and it cascaded through the air alluringly.

“Okay, bow number two; the boob bow,” Katherine commanded. “Then I’ll go and leave you two lovebirds alone, but I just want to see a bit of my handiwork first. Though I must add as an aside that next time I hope I’m invited. You know it is after midnight, nudge, nudge.”

He answered, “I’m aware, and that makes me even more impressed by your generosity.”

Midnight meant the end of Saturday, which technically meant that he now allowed himself to fuck his sister at home, even though they would still be going behind their mother’s back about it. “You will be included, soon, but you know how it is, wanting to be alone for the first time.”

Katherine nodded with some resignation and regret.

He undid the second bow, and Amy’s boobs, already mostly uncovered, sprung free and jiggled around.

Amy languidly lay back on the bed, raising her bound hands up above her head.

He was entranced by her beauty, and by her subjugation that was symbolized by the tied wrists and ankles.

“I’ll leave you be to work on bow number three, the pussy bow.” Katherine made to leave.

“Thanks so much, Sis,” he said. “Little Pincer Cunt Walls of Death Sis. This is a really nice gesture.”

“Yeah, thanks, Kat! You’re the awesomest, super best friend!” said Amy enthusiastically.

Katherine waved off the compliments, even while she was obviously happily eating them up. “I’m trying to cure myself of the jealousy Xania so dramatically demonstrated that I have, plus I really am happy for you. You’re better than my best friend. Just think of all the great threesomes we’ll have together now!”

Amy agreed, “Yeah! Cool! We’re BESTEST best friends, aren’t we?”

Katherine was starting to get a little teary-eyed. “We are! I just know we’re gonna have so many good times together, Amy, cheek to cheek while sharing Brother’s cock.”

“Totally!”

“But enough about me. Have a good night.”

Katherine entered the room to give Amy a brief but heartfelt kiss on the lips. Then she gave Alan a sweet gentle goodnight kiss on his cheek. She explained, “I can’t do anything more than that, because if I get started I won’t be able to stop. Have fun, you two!”

With that, she left and closed the door behind her.

Alan turned around and focused on his horizontal girlfriend. “Okay Aims, it’s just you and me. This is all so romantic, don’t you think? I’m so glad I waited a bit until we could do it right in the right setting. Why don’t I just lie on top of you and kiss you for a while?”

“M’kay!” She paused, and then added, “Actually, Beau, don’t ask me what I want, because I have no say in the matter. I’m all tied up, and my neighbor, the big bad Alan wolf, he’s going to take advantage of me!”

Alan watched her writhe around in mock anguish. His dick got as hard as it had ever been, which was saying quite a lot. It didn’t matter that he’d had so many intensely sexual experiences earlier in the day; he had the remarkable ability to put all of that out of his mind and live in the moment. Right now it was just him and Amy and nothing else in the world mattered one bit.

He admired her slowly writhing body as long as he could, attempting to burn the image into his mind for all time. Finally he could take no more, and fell on top of her. He practically attacked her, as his hands were everywhere at once. They kissed for several minutes.

However, Amy couldn’t put her arms around him because her wrists were still tied up by a bow.

Alan rather enjoyed her helplessness, wondering whether that enjoyment implied that he might eventually get into S&M sex. But he also wanted her hands available to do more, so he said, “I’m going to undo the rest of your bows, okay?”

“‘M’kay!”

He freed her hands first, then her ankles. He undid her pussy bow last, leaving her totally naked except for high-heeled shoes and a smaller bow around the neck.

He said, “Aims, I must admit, I’m too excited for much more foreplay. Let’s just have sex.”

“M’KAY! I’m ready and like, totally soaked! I want you to fuck me! Stick it in!”

“All right, here it goes.” They didn’t need to use a condom since she had been on the pill since the start of the semester. Lying on top of her, he pushed his meaty shaft into the eager, wide-hipped girl.

She cried out, “Oh, oh, oh, oh, OOOOHHH!” Her scream “Aiiiieeee!” carried through the walls like they weren’t there and was heard throughout the Plummer house.

He had considerable difficulty pushing his boner into her. Of all the women I’ve fucked so far, she definitely has the tightest pussy. Dang! He tried to get his cockhead in, but it seemed like it was simply too big to fit.

Finally, with a great thrust, he got the wide bulbous head through. But there was still considerable resistance. He paused and asked her, “Does it hurt?”

Panting, she admitted, “Yeah, kind of. But that’s okay. In the movies it always hurts the woman first and then it gets better.”

“But you’re not a virgin,” he pointed out. “There’s no blood.” He added with growing horror, “Don’t tell me that’s from the time you were raped!”

“No,” she admitted. “That dumb Jack Johnson was a big loser and a stupid fathead, but luckily he never got very far with me. His hands were all over me like an octopus, but not in a good way like when you do it, you know? I kept yelling ‘NO!’ louder and louder. Luckily, someone came quickly before he could do any more than attack my boobies. So you’re really the first. Maybe it just takes some getting used to.”

Despite the seriousness of the discussion, Alan found it endearing that “stupid fat head” was about the severest insult Amy could muster. He said, “Let’s not talk about that unpleasantness. Let’s just have fun.”

He pushed in again, unsuccessfully. Then something occurred to him. “Hey Aims. You never really explained how you lost your virginity.”

She giggled. “Oh. Beau, you’ll always be my second love. My heart really belongs to my first love, my hair brush!” She laughed even harder.

He laughed too. He was also greatly relieved to get confirmation that things were taken care of, since he became very squeamish around blood.

They quickly grew serious again. Both were eager to get down to some serious fucking.

He already had his cockhead in her but found her vagina so tight that it was tough going all the way. He raised himself up as if doing a pushup over her, then lowered his whole body. As a result, he slowly skewered into her the rest of the way.

At first he worried that it might have hurt her, but then her excited “Woo-hoo!” quickly put that concern to rest.

Then he resumed sliding in and out of her. She still screamed like a banshee, and he still had the sensation that he must be hurting her, if only because she was so tight. Lubrication certainly wasn’t an issue because she was plenty wet; her pussy was simply tighter than the other orifices he had experienced.

However, after a few minutes the going began to get a little bit easier and his fuck started to get a lot more pleasurable. Her vaginal walls had a wonderfully velvety grip on his erection, but they no longer seemed to be squeezing it to death.

He hoped that she was enjoying the fuck as much as he was. He was about to ask her feelings when she shouted, “YES! It’s just like the movies said! It feels good now! Way good! Gosh, Beau, keep doing it! Totally! This rocks! Fuck me more!”

He kept fucking her. He was surprised that, given how quiet and passive she normally was, she was so loud and active. She squeaked, moaned, or gasped with his every thrust.

He’d expected for her to lie there while he directed the actions and did most of the work, but she soon became as physical as he did. In fact, after a while she rolled him over and pumped her hips up and down over his cock while he just lay there. Her entire body rose and came crashing down onto his, over and over again.

He was glad, because it seemed he was forever having to ration his sexual energy. Plus, this way he could impale her all the way to the deepest depths of her pussy with every stroke without even having to move his hips.

He greatly enjoyed the fucking, but he was also somewhat disappointed in one respect, because her sexual skills were so far below Suzanne’s, and those skills were fresh in his mind from what they’d done that afternoon. For instance, Amy didn’t squeeze with her vaginal muscles at all, and she didn’t know his needs or have a sense of timing. But he’d been aware of this before he started and enjoyed the experience for what it was.

Her mother Suzanne, for instance, excelled at squeezing him with her vaginal muscles, and knowing his needs, and timing things just right. He realized though that it really wasn’t fair to compare. Aims will have lots of opportunity to get better, and I’m going to be the one to teach her. She certainly doesn’t lack enthusiasm, and her pussy is so remarkably tight! Actually, if she learned how to do the Suzanne squeeze thing, she’d probably snap my dick clean off! Ouch!

Amy was truly filled with enthusiasm; there was no denying that. However, to listen to her, it sounded like suffering. Even her panting and moaning made it sound as if she was being slowly tortured. Her face had torturous expressions at times, too. But at other times it was a face of pure ecstasy, or some combination of suffering and joy.

However, while Amy wasn’t that skilled, she didn’t completely lack clever surprises. Alan had been happily thrusting and huffing and was about to climax when all of a sudden she came to a complete halt. Since she was sitting on top of him, he had little choice but to go along with what she wanted to do. He tried thrusting up into her since his shaft was still buried deep inside her, but that didn’t provide enough stimulation.

“What?!” he complained with great exasperation. “Why did you stop?!”

She giggled. “I’m just pulling an old Alan trick. The infamous strategic break.”

“Not now!” he wailed.

That only caused her to laugh some more. Then she said, “Hey, if you can do it, I can do it too. I’ll tell you though, it’s so hard to stop once you get into that rhythm. You know? It’s like a primal thing, an irresistible urge to keep on going.”

“I DO know! Amy, resume fucking right now! That’s an order!”

She just laughed some more. “I’m really digging this woman-on-top thing. The woman’s got the power, hee-hee!”

He growled.

“Oh, oooo-kaaaayy…” she mock sighed. She resumed repeatedly impaling herself. “You have to admit, it’s a lot better to draw it out some.”

Before long, they were again going at it at full speed. But, to Alan’s surprise, the more they fucked the more energized he felt. He decided to take charge instead of having Amy do most of the work. He suddenly pulled her torso down to his chest and rolled both of them over so he was lying on top. Then he began banging her in the missionary position.

She seemed to like that a lot, and also became more submissive in her attitude. Even though she was puffing like a steam train, she somehow managed to blurt out, “Take me! Take me, lover!” Then, after some more huffs, she managed a final, “Take my cunt and OWN IT!”

That aroused him a lot, so much that he came before either of them were ready.

However, he was too naturally talented a fucker to let the lack of a mutual climax ruin things. He pounded into her hard, shooting ropes like a machine gunner firing bullets with reckless abandon. Cum seemed to be flying everywhere, filling her pussy to the brim.

Then, when his climax finally ended, he kept going. He fingered her for another minute to make sure she’d cum too.

Amy loved it; she squealed like a stuck pig. Not only did everyone in the house know exactly what had happened, but there was a good chance the rest of the Pestridges next door could hear it, too.