6 Times a Day

Alan meanwhile found himself with the strange chore of having to masturbate six times a day, rain or shine. He set himself a schedule, and followed it for the next six days. He managed to keep his masturbation sessions completely private and no one said anything, to his great relief.

His family was so shy about talking about such things that the additional discussion they should have had about his situation was put off until the next day, and then put off again, and again.

It required Suzanne to be the initiator for this kind of thing, but she thought, I'll wait a few days, so the others can begin to get a sense of what six times a day really means. Then I'll be able to steer the talk and action better. The more time that goes by, the more receptive the others will be to my naughty ideas.

During this time, things in the Plummer house slowly started to change. It gradually dawned on everyone that Alan would likely need help to maintain his six-times-a-day pace - a lot of help. Even if he did get himself a girlfriend, which seemed extremely unlikely, chances were that person wouldn't be able to help enough.

Suzanne, of course, had been hoping for that realization all along.

On a conscious level Susan was still oblivious, though on a deeper level she was starting to see her son in a sexual way. She continued to wear the same prudish, conservative clothing as always, complete with her white hair ribbon and bookish black glasses. She had a fantastic body, but she seemingly did everything she could to cover it up.

The one other person who was often at the Plummers' house, Suzanne's daughter and Katherine's best friend Amy, had not been informed of the changed situation, because her mother Suzanne had a hard time thinking of her in a sexual way and so had made sure that Amy didn't know what was going on.

That left Katherine, who had a secret she'd buried so deeply that not even the very perceptive Suzanne had realized it: Katherine lusted after her brother.

On the surface, this seemed very unlikely. What would one of the school's beautiful new cheerleaders find arousing in her nerdy and sexually clueless brother? But Suzanne wasn't the only one who'd noticed the recent changes in Alan's body. All that swimming and tennis had done him good. Furthermore, Katherine just loved him all around as a person. They'd pretty much been best friends since they could talk. She always found herself comparing the boys she went out with to her brother, and the others always came up wanting.

As a result, she had little interest in other boys. She'd gone on a few dates, mostly because it was what she was expected to do: cheerleaders didn't just stay home every night. But she continued to dress conservatively, mostly out of some sense that she was keeping herself for Alan. For the same reason she also didn't do anything sexual on her dates beyond a simple goodnight kiss.

Yet at the same time, she was deeply ashamed by her desire for her brother because she thought that he would never reciprocate. Her low self-confidence was a big reason for the depth of her pessimism. But she also figured that even if he did, to actually get intimate with him would break their mother's heart. Even if her mother Susan never found out, Katherine loved her mother so much that she would have felt terribly guilty about what her mother would think if she did. All of this left her extremely conflicted and frustrated.

But now, with Alan's medical diagnosis, Katherine began to realize that she might have an excuse to get sexually intimate with him under the guise of helping him cum, and her mother not only might not get upset, but might theoretically even approve of the idea.

It was all still very tentative, but ideas and fantasies began to form. She'd always dressed conservatively at home as well as outside because she'd been trying to suppress her impossible love. But now she started to dress a bit more provocatively.

Previously, she'd made a conscious effort to hide her luscious body around her brother, because she figured that if he started lusting after her, it would only make her own lust harder to bear. Even though she frequently swam in their backyard pool to stay in shape, she went out of her way to only swim when he wasn't at home or was taking his usual afternoon nap.

But two days after he started his masturbation schedule, she lingered in their pool until a time when she knew he would get home. It so happened that Alan also wanted to take a swim, so she kept herself inconspicuous until he stood just a few feet from the pool, and then she pulled herself out of the water with a big splash so there was no way he could miss her anymore.

"Sis!" he exclaimed. "What are YOU doing here?"

She stood before him, dripping wet in a dark blue one-piece bathing suit. "Um, I live here," she giggled. "And I believe it's called 'swimming in the pool.'"

"I know that, but geez... I mean, it's just..." He couldn't figure out how to say what he really wanted to ask her, which was why she was violating their unspoken but well-understood rule of not showing any "skin" around each other.

Even though her one-piece bathing suit was extremely conservative by Southern California standards, it showed off much more of his sister than Alan was used to seeing. Her slick wetness and hard nipples jutting through the suit made her look even more desirable than the few times he'd seen her in her cheerleading outfit. Besides, he usually saw her in that outfit from a distance, but now she was standing just a few feet away.

Virtually the only time he'd ever seen her in a bikini, and then from close-up, was when Amy had gotten Katherine and him to pose for sketches she was doing for her art classes to improve her understanding of human anatomy. Usually, Amy would pose just him alone, or just Katherine alone, but sometimes she would insist on having the two siblings pose together, or sequentially in the same sketching session. On those occasions Katherine and Amy would both wear skimpy bikinis that Amy had selected, which gave Alan the opportunity to furtively ogle the two girls for a couple of hours. Unfortunately, that opportunity had ended with the last school year, along with Amy's art class in life drawing that required her to make such sketches.

His dick grew erect, leaving him with the big problem of trying to hide the bulge from her eyes. Rather than standing there talking, he decided on quick action and dove into the pool.

Katherine was amused and flattered at how flustered he was. She was even more flattered to see the outline of his erection before he launched himself into the water. She immediately resolved to show herself off to him a lot more in the near future.

As Alan swam, he looked back and peeked at Katherine drying herself off with a big yellow towel by the side of the pool. He thought, I've tried so hard - for years! - to not think about Sis or Mom in a sexual way. God knows they're both gorgeous enough. Too gorgeous. And now this. Sis not only didn't scurry off like I would have expected, but she was practically flaunting her stuff as she stood there almost defiantly in front of me. Is she trying to help me with sexy material for my frequent masturbation needs? Whoa!

Maaaaan... I hope this doesn't mean I'm going to have more incestuous dreams. I hate it when that happens. These days, I always seem to wake up to a wet spot. It's a good thing Mom still just takes care of my sheets without trying to talk to me about it. Thank God, 'cos otherwise we would both die of embarrassment.

He looked over to where she was still drying herself off. Dang! Sis is built! I just pray she's not showing herself off on purpose to help me out with my new medical treatment. If she is, I'm so screwed. I can't allow myself to think of her or Mom in that way. I can't!

But the next day, nearly the exact same thing happened when Alan came home and again wanted to go swimming. She was there in that same bathing suit, dripping wet and looking fantastic. He couldn't help but get extremely aroused and embarrassed all over again.

He knew something was up for sure, but he still couldn't figure out how to talk about such an awkward subject.

— — —

The next night, four nights after Alan's diagnosis, Alan burst into Katherine's room to ask her a question. Her room was right across the hall from his, and since he'd heard music playing he hadn't bothered to knock. "Hey, Sis," he started to say, but then the words stuck in his throat.

It was only an hour after dinner, but she was already wearing just a nightgown. And it wasn't a nightgown that left much to the imagination. It was white and transparent enough for him to clearly see the outline of her nipples. He would have seen her bush as well except that when she stood up to greet him her movement bunched up the fabric in front of her crotch.

She smiled at him. "Yes? Cat got your tongue?"

He blushed. "Um, no, er, well, uh..." His flaccid penis rocketed into full erection within seconds. He was more worried over how he could adjust his shorts to cover up the blatantly obvious bulge that had formed there than he was about thinking of what to say.

She giggled. "Something wrong?"

Suddenly he blurted out, "I'm so sorry!" But he couldn't stop staring. Dang! Sis is HOT! And... Shit! I can see her nipples and everything! This is a thousand times worse than seeing her in that blue bathing suit. DAMN!

"Sorry? What for? Your face is turning all red. Oh, I know what it is. You're probably not used to seeing me dressed in something like this."

"No," he squeaked out. "No, I'm not."

She giggled some more. "I guess I'm flattered then. You don't mind, do you?"

He shook his head 'no' vigorously. Otherwise, he continued to stand there like an idiot, wondering how obvious his erection looked and if his sister had noticed it yet. He was slowly trying to put a hand in a pocket without calling attention to his movement. Shit. I'm so in lust right now. This is probably gonna cost me years of therapy when I'm older, but I can't help it! Sis is a smoking-hot cheerleader, and she's so close to being naked!

She giggled. "I'll take it that you like." Seeing him nod just as enthusiastically, she smiled, and then turned a bit more serious. "The thing is, I was thinking... It's kind of odd for Mom and me to dress like nuns when you're spanking the monkey every hour, don't you think?"

He was shocked. "Sis! What did you just say? Are you trying to humiliate me?"

"No! Not at all. You know I'd never hurt you. That was just a bad attempt at a joke. Sorry. But it's still a fact, isn't it? If you're gonna loosen up sexually, why can't I? We're becoming adults. Why do I always have to dress like I just stepped in from a blizzard? Frankly, this is a lot more comfy." She turned a little bit, showing off her curvy side profile.

"Um..." He didn't know what to say. "Good point," he finally managed. He wanted to tell her that she didn't have to try to help him with visual stimulation, but he was too shy to talk about it.

Eager to change the topic, he sat down in a chair and asked the question he'd come in for. In the process, he also managed to hide his erection by sitting down. He left shortly after that.

But Katherine hadn't missed his big bulge, not by a long shot. When he'd gone, she thought, A-ha! He DOES find me sexy. It's just a matter of how I dress. Or not dress, hee-hee! Cool! I just love giving him those insta-boners.

But then she paused and thought, But where am I going with this? Aren't I just torturing myself, bringing myself closer to what can never be?

She answered her own question: True, but this isn't just for me. I'll bet he goes back to his room and DOES spank his monkey. And maybe that helps him reach his six-times target a little bit easier. Isn't that what family is for, helping each other out when in need? If he was sick, I would help with picking up his homework and his chores. This whole six-times thing has to be hard on him. It is a medical treatment after all. I HAVE to help my brother out.

She waited a few minutes before sneaking across the hall to put her ear against her brother's door. She couldn't hear anything, but then she got a cup and put it to the door and her ear to it. Sure enough, she just barely made out a dull rhythmic thumping.

— — —

Flush with that success, she made it a habit to dress very casually before school, where she might run into Alan coming from or going to the bathroom. She wasn't worried about their mother Susan seeing her, since her parents' bedroom had its own bathroom. She did the same after dinner where, again, she was unlikely to run into her mother. In fact, two nights later, she took things a bit further by again playing music on her stereo after dinner, hoping that Alan would come into her room for some reason or another.

Eventually he did, but he was usually a well-mannered kid so, remembering what had happened the previous time, he was careful to knock.

Katherine sprang into action. She stood up and began undressing.

Alan, assuming from the music that she had to be awake but probably on the phone since she didn't respond, just walked in. He caught her in the process of taking off her lacy, partially transparent underwear. (Actually, she'd been waiting in that position until she heard the door open.) He was mortified at violating her privacy like that.

But she acted like there was no problem. She hooked her bra strap back on her shoulder and pulled up her panties as she replied, "Oh, hi Big Bro. I didn't hear you there. What's up?"

"Oh sorry! Geez."

She joked nervously, "We have to stop meeting like this."

His eyes practically popped out of his head, because even after her undies were in place, they were semi-transparent. He had a startlingly good look at her dark bush in particular.

Suddenly, he was so aroused that he couldn't breathe. His heart beat like a hammer. "Oh man! I'm soooo sorry! Really, really sorry. I'd better go." He turned and started to close the door.

But Katherine said, "Hold on! Where are you going?"

Alan froze and turned back, but he kept a hand over his eyes like she was the sun and he was trying to prevent himself from going blind by staring in her direction. "Um, I just had a question. Sorry for barging in like that. I'll go now."

She giggled, pleased at his chivalry. But she barked, "Nonsense. Take your hand down, unless you think I'm too ugly to look at."

"But you're wearing undies," he protested. The fingers on his eyes were spreading just a bit, allowing him to peek through some.

"So? You could see more of me in a bikini. So what's up?"

Alan took his hand away and tried in vain not to stare. He couldn't help but focus on the dark marks on her ample breasts, allowing him to know just where her nipples and areolae were.

He couldn't figure things out. She had never worn revealing underwear like that before, nor did she wear nightgowns like the one she'd had on a few nights earlier. He wanted to mention that while he might have been able to see more of her in a bikini, she never wore a bikini around him. Strangest of all was that she didn't mind him staring at her. Though he couldn't find an explanation, the more he thought about it and the more he looked, the more aroused he became.

She pointed out, "Recognize the song? 'You're My Best Friend' by Queen. Pretty appropriate, huh?"

"Uh, why?" He was too horny to think straight. She was letting him ogle her body freely, acting like she didn't notice where he was looking.

"Because you're MY best friend, you doofus! Weirdo, silly doofus!" She giggled.

He tried to think coherently and act normal. "And you're my best friend too. You're really great. But that doesn't mean you have to... Uh, I mean, you don't-"

"Don't what?"

He wanted to tell her she didn't have to dress enticingly to help him out with his frequent masturbation problem, but he was too shy to bring it up. Instead, he said, "I didn't know you like Queen."

"I don't really, just a few songs. This one especially."

And so they talked about music and other things while Alan again tried to hide a raging erection. Only now was it starting to hit him what a gorgeous sister he had.

Swimsuits and pools played a big part in Katherine's new efforts. It seemed like almost every time he went for a swim, she was right there.

It was a gradual process, but he was starting to see her in a new way. True, he'd secretly lusted for her in the past, but he truly had fought it. She was always so bundled up that he could keep his forbidden lust in check. But now, Katherine was on display so frequently and so impressively that he found it harder and harder to get her out of his mind. In short, she was wearing down his resistance.