6 Times a Day

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William Osborne, Jesse Boyer

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Danial Haxton, Tangents, JustGotHit, Killstroyer, WendigosArk

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Katherine finally decided to take the plunge and say what she'd been meaning to say. "Getting back to what I was saying before, yeah, some of my friends not only have submissive fantasies, but they actually get to act those fantasies out. Especially the ones who are lucky enough to have sex with Alan. He does all kinds of stuff; he instinctively knows exactly what each girl wants. Or I should say, what she needs. If a girl needs to be spanked, he can see that right away, like it's written on her face. If you were to become one of his sexual helpers, I'll bet he'd have you naked and bound in no time."

Christine's eyes looked like they would pop right out of her face. Her nipples were already quite hard, but they seemed to visibly grow even longer after Katherine said that. Her pussy was lubricating freely and she didn't try to fight it. But she still held back from completely admitting what she wanted, even to herself.

She said, "Wow. Well, that's interesting, Katherine, but there's a big difference between fantasies and reality. If I was ever with him, you know, in that way, and that's a big if! A huge IF! But if I was, I'd be perfectly happy with the vanilla stuff. These are just dreams I'm having. More like nightmares, really. I'll be damned if I'd let anyone treat me like that in real life. If they tried it they'd be in a world of hurt. I'm not some kind of pervert! Oops, no offense!" In an embarrassed whisper she asked, "Have you ever done that, uh, kind of thing, for real?"

"Me? I wish, but no. I think the only guy in this school who would really act out fantasies like that is Alan, and of course he's my brother. When I hear some of the things he does with other girls though, I'm amazed. But they all love it." She was trying to build up Alan's sex appeal at every opportunity.

Christine was downcast all of a sudden again. "Whatever it is he'd do to me, I'm sure it would be great. But I've already given it my best shot to get him interested. I've laid it all on the line, and he wasn't interested. Not even slightly."

With an uncertain face, she looked imploringly at Katherine and asked, "Is there something wrong with me? Do you think, well, do you think that someone like me could... um... Is it my personality?" She looked down at the floor in embarrassment. Again, her lack of sexual self-confidence was apparent.

Katherine could see her intended meaning. "You're asking do I think he'd find you attractive enough? The answer is: certainly! He asked you out for real less than two months ago; I'm sure I don't need to remind you of that. You were the FIRST girl he asked out, ever! He's been moony for you for ages. Of course Alan has extremely, extremely, EXTREMELY high standards these days. Word has gotten around lately that he's a sensitive guy who nonetheless screws like Superman in heat, so a lot of girls have been throwing themselves at him and he's turned nearly all of them down."

"I was such a fool!" Christine blurted out. She recalled bitterly how she'd rejected Alan's date invitation a couple of months earlier, in part because of selfish concerns about his low social status. Now he had become quite possibly the top catch in the school, as well as the only guy she really liked, and she'd thrown that all away.

Katherine ignored Christine's outburst and continued, "For him to be interested in a girl, she's got to have an incredibly fit body and jaw-droppingly stunning face. But that's not enough. The main thing for him is breast size. E-cups at the very least. People call me attractive, but even I could never come close to meeting his bare minimum requirements, since these barely qualify as D-cups." She looked down at her chest sadly.

Katherine hoped this fib would go a long way towards deterring Christine from having any suspicions of incest. She added, "You, on the other hand, you have everything he desires in a woman's body. Since you're one of the few to qualify, that means you don't have much competition. The only problem, from what I understand, is he needs to get over some emotional issues, for instance a fear that he could find himself so attracted to you that it could hurt his relationship with Amy. But I can help with that and smooth everything over, if you want me to."

"Oh yes!" Christine replied eagerly. Then realizing she'd been far too eager, she added with pretended detachment, "That is, if it's not too much trouble."

"No trouble at all! I can bend his ear and Amy's too. In the meantime, you need to go all out to make yourself completely irresistible to him. Maybe if you just dress a little more to show off..."

"You think?" Christine hefted up her boobs as if inspecting them for the first time. She looked down at them with a puzzled expression, as if wondering what the big deal was with those two bothersome blobs of flesh.

In her opinion, having a big rack was nothing but trouble. She got attention from guys, yes, but the wrong kind of attention from the wrong kind of guys, the ones who only saw her as a piece of meat. Other girls were both intimidated by and jealous of her outrageous endowment. Her heavy breasts caused her back pain and got in the way of her sports and martial arts training. She went to great lengths to cover them up and de-emphasize them, but they were so big that she was never completely successful in doing that. Guys very literally couldn't seem to look past them. She'd even caught her own father stealing a glance or two at her cleavage, which disgusted her to no end. Given a choice, she would have preferred to be svelte and trim rather than so curvaceous and buxom.

"I guess they are sorta big," she muttered. "But apparently they aren't enough for his tastes. Alan hardly looks at me..."

 However, Katherine was mentally on a completely different planet. Seeing Christine heft her F-cups like that, she was immediately transported into a fantasy where Christine was wearing the "Alan uniform" - naked except for high heels. In her fantasy Christine was a full member of Alan's harem and was raising her boobs for his inspection.

In Katherine's daydream Christine said, "Master, please, don't you like them? Now all you do, it seems, is fuck Kat all day long, while my tits grow so lonely and unloved. Please, Master, fuck them hard! Shove your long pole right through my cleavage and into my mouth! I've been dreaming about your sweet taste all night; it's all I can think of!"

In Katherine's fantasy Christine continued to plead, "Or if you've cum too many times today, how about you, Mistress Kat? Can I offer them, and the rest of my horny body, for your pleasure? I know these things don't measure up to your remarkable G-cups ever since you started lactating for the baby, but still, they're here for you to squeeze and suck on! ... Can't I at least lick Alan's stiffness together with you and Amy? You know how Amy's mother always says that three tongues at once are best. Alan, don't neglect your Number Five Fuck Toy!"

Katherine was so turned on by this fantasy of having access to Christine's body as part of Alan's harem (though in the dream it was more like Alan and Katherine's harem), that she practically had to prevent herself from drooling openly. It confirmed for her that her decision on how to deal with Christine, based on what she'd learned thanks to her lucky Wonder Woman guess, was the right choice.

But outwardly she showed little sign of her debauched daydreams. She replied fairly quickly and decisively, "I know I'm right about this. Let's get together and talk fashion soon. That'll be fun. But as I was saying, Alan has quite a few amazing and completely devoted lovers. He's had a few one night stands, but most of the time, if the woman passes his standards, like you definitely do, he likes to please them on a regular basis."

Christine was wowed. "God, you make it practically sound like he has a harem or something."

Katherine was going to say more in her enthusiasm for her brother's sexual skills, but that comment made her realize that she'd probably said way too much already. She hadn't meant to all but say her brother had a harem. Furthermore, she realized she had to be careful not to give away her own incestuous feelings. She hoped that her "possessive" cover story could help cover any small mistakes she might make in the future in that regard. She stammered, "Yeah, well... People do joke, but you know..."

But Christine was so worked up that she hardly paid attention to that. She just asked with curiosity, "Really? I mean, do you think... Well, this sounds kind of outrageous, but is it possible that I might really be one of Alan's helpers? Wouldn't Amy mind, particularly if he had sex with me a lot?"

But as soon as those words came out of her lips, she backed off from them. "Oh my God. What am I saying? How absurd! The very idea, it's so demeaning. The whole school would be scandalized and think that I'm some kind of... And my parents. God, my parents would FREAK! Sometimes I think that's what I want but I really shouldn't. Please forget I asked that!"

However, Katherine decided to ignore Christine's reservations. She figured that if she'd made it this far without getting punched or slapped, she might as well try to open Christine up more to the idea of sharing Alan, with the ultimate goal of having her accept a place in his harem.

To be truthful, Alan hadn't asked her to do that. In fact, he'd adamantly denied wanting Christine at all the night before. But Katherine assumed he'd think differently if he knew of the clever scheme that had all but fallen into her lap, thanks to Christine's unexpected revelations.

She decided not to tell Alan about any of it just yet, though. She figured he'd enjoy and appreciate it more if she could present a submissive Christine begging to be royally fucked as a done deal. She considered giving him surprises like that to be part of her role as an "uppity" sex slave and fuck toy. She should know her master's heart better than he did, and know when his "no" really meant "yes" and vice versa.

So she said, "Don't worry. As one of his helpers, he'll have sex with you so much that it'll be like he's your boyfriend and then some. He's incredibly virile, you know. At least, that's what they all say. I'm sure it won't be a one time deal either, not with the way he feels about you. As his sister, I saw him pining away for you for so long that it was practically embarrassing. When you rejected him so thoroughly, he was so crushed about it that he turned to Amy and she welcomed him with open arms. It's true that I helped them get together, but it probably would have happened anyways. But you were the one he wanted first. You, and at that time only you."

Christine was torn, but really she was playing devil's advocate to her own feelings. She wanted Katherine to sell her on the idea of being a "helper" to help put her own doubts to rest. She said, "I don't know..."

Katherine could sense what Christine wanted and said with great enthusiasm, "The thing is, he's so sexually insatiable, yet at the same time he has such a big heart! Haven't you heard of people playing the field before they announce they're ready to go steady? Well, Alan's kind of like that except he's sort of playing the field and going steady with Amy at the same time. He has so much love to give, in more ways than one, that Amy knows that he's too much for her to handle alone. As his sister, living just down the hall from him, I'm totally amazed at the women I've seen come and go from his room these past two months. Yet each one has left completely satisfied in every way. Their bodies AND their hearts, completely satiated. He's just such a nice, sensitive guy! You couldn't pick a better man on Earth to be your first lover. I know he'll make it a memory to last a lifetime."

"Hmmm." Christine was still torn between being morally outraged and being sexually intrigued. When it came to sexual matters her complete inexperience repeatedly caused her to get cold feet. She made the vague statement, "You have to admit, it's a damnably odd situation. And I find it even stranger talking it over with you, his sister. But let's just say, totally hypothetically, that I did become one of his so-called helpers. What if Amy and I wanted to be with him at the same time?"

Katherine looked at the signs of Christine's high arousal and decided to take a risk. The true answer was that Amy would come before Christine in that kind of situation. But rather than admit that, she leaned forward and whispered conspiratorially, "Let's just say Alan can handle anything. Two at once is not a problem. It's one of the reasons that Amy doesn't mind sharing."

Christine's mouth dropped open and stayed that way. She was beyond scandalized, again. She thought, Is she saying what I think she's saying?! Do all of his helpers share him? How does one boy even have sex with more than one girl at a time? True, I could see more than one hand or tongue on him at a time... My God! That's just so... sinful! Naughty! Would I have to do that?

Would he force me to? Would I even have to do things with Amy? With other helpers?! That's so wrong that it's probably a sin just thinking about it. I really need to know what I'm getting into here. But it's so embarrassing to bring that up. What if they all have sex together in some kind of depraved, giant orgy?! How am I supposed to ask about that?

I just want him to take my virginity, that's all. Really! I'm really not looking to become some kind of, well, I don't know what to call it. Depraved, sex-mad slut? This new Alan is so sexually overpowering that it scares me. What if I lose all control and let him turn me into some kind of sex pet, like what happens in too many of my dreams lately? If I have a lick of smarts left I need to steer clear of him altogether. That's what I should do. Definitely!

 However, her body betrayed her thoughts as her arousal steadily increased. In particular, the idea of being forced to share Alan's erection turned her on more than she could admit even to herself. She vividly imagined herself and Amy sucking and licking his erection at the same time, their mouths nearly touching in the process. The idea of sharing also reinforced her growing belief that he was so virile that one woman alone wouldn't be enough to satisfy him.

Katherine again realized that her comments had come too close to exposing her incestuous feelings and her place in Alan's harem, so she was quick to keep the conversation moving. "But don't worry about that now. The important thing is that you need to convince him to make you a woman, fully and completely. That's going to take some work. You'll need to stay your same self for everyone else, but become a sexy, flirty, teen dream for him."

Christine volunteered, "There's some good news there. On the non-romantic dates I've been having with him, we've been practicing flirting and I'm getting the hang of it." Suddenly she was reminded of Katherine's spying on their latest date. She added in a chagrined and irritated voice, "But you know that already, don't you?" She was amazed at how much their conversation had evolved since Katherine's confession of spying.

Katherine quickly responded, "Sorry. But I promise I'll make it up to you, big time! One thing I want to do is give you a makeover. You should keep your sexually innocent aura going, yet at the same time come across to him as sexually knowing."

Christine was so excited that she was unusually quick to forgive. She said, "There's more good news on that, too. The other day a, uh, friend, helped me pick out some kind of 'sex for dummies' books. I've been reading them off and on at night, after doing my homework assignments, and learning a lot."

Katherine replied, "Good. That's a great start. But you can't learn everything from books." She suddenly had a vision of Christine practicing cocksucking on a banana and then doing the real thing between Alan's legs. It got her very sexually excited.

She realized that she was already thinking of Christine as one of the group instead of an external threat. As a result, she found her jealousy had suddenly greatly decreased, though not disappeared altogether. As she thought about that, she had to remind herself that it was far too early to let herself feel that way. She further had to remember that Christine was still dangerous and the plan to get her to change was still just that: only a plan.

She continued, "This could be fun! I can help you undergo a secret transformation. I say secret because at school I have a respectable reputation and look; you've seen how I dress." She waved a hand over her clothes. "Very respectable. But when I go out on a date with the right guy, I can be a wanton sex kitten. The key is finding guys like Alan who are completely discreet. If you're smart, you can maintain your reputation and status at school while fulfilling your every sexual fantasy in private."

She went on, "And you know what? I'll bet I can get Amy to help out since she's my best friend. After all, I'm hardly the right one to ask about all the details of what he does in bed and how he does it. As his sister, my position is a bit awkward on this, all around. It's much better for you to talk about certain things with Amy. She can give you the inside scoop and tell you exactly what he's like in bed. Lately she's clammed up about Alan and his incredible sexual prowess, because that's led to trouble with the football players, among others. But if I ask her, I'm sure she'll make an exception and talk to you."

The words "incredible sexual prowess" rolled around Christine's brain. If Alan was simply too much for one woman to handle alone, that could give her an excuse to avoid being morally offended by the situation, allowing her to have sex with him even as he dated Amy. Yet at the same time she found the whole idea of him being that sexually demanding extremely arousing (probably because they played into her nighttime fantasies).

She was about to ask who Alan's other girlfriends were, but hearing the words "football players" reminded her to scan the halls again. This time, she saw two people just as they got to the top of the stairs and came into view.