SIX TIMES A DAY – Part 12
Paint It, Black
Day 33: Friday, October 18
Copyright © 2004 - present Spacer X; All Rights Reserved.
This is part of a longer e-novel. It's highly recommended that you start with the Introduction and read the parts sequentially, in order to understand the characters and previous events. The Introduction also provides the full set of story codes for all parts, as well as explaining the story structuring into chapters within parts.
This is an illustrated story. If for some reason a picture doesn't display, you may need to refresh the page or right click on that particular picture to retrieve it. If a picture has a black border, then there is an alternate version showing more skin. Read the "Bonus version" instructions in Artwork to activate and use this feature.
Alan woke on Friday morning feeling uncertain. He didn't know whether to expect the "new" Mom or the "old" one, and the return of Ron loomed ever nearer. To be safe, he masturbated twice in his room when he awoke, so he'd at least start on his daily climb toward six times.
As it was, Susan was definitely in a prudish and conservative mood, so Alan was careful to be on his best behavior. He didn't say or do anything that could be construed as even slightly sexually provocative.
But that same morning, Katherine soon found herself with a very big problem. She had continued to go without bras and panties, dressing as scantily as Susan would allow. She was having so much fun with Alan that she didn't want it to end. She had put on her cheerleader uniform because there was a football game that afternoon, and the cheerleaders wore their uniforms all day long on game days to help build school spirit.
At breakfast, she had flashed her pussy at her brother, so it was bare under her very short, red cheerleader skirt. The danger of getting caught by her newly stern mother who was cooking breakfast was great, but that just added to the challenge and the excitement. She did manage to catch Alan's eye with her stunt, and succeeded in getting some reaction out of him, despite his glum face.
But the underwear cabinet next to the front door was now gone in anticipation of their father coming home, so when she left she forgot to wear her panties.
It wasn't until she was about to enter the school building for her first class when she felt a breeze between her legs and realized, Oh God! I don't have any panties on under my cheerleader skirt!
She immediately snapped her legs shut, wondering in fear if anyone had noticed. She looked around and decided that no one had, as she'd just stepped out of her mother's car a few minutes earlier. She decided she had no choice but to go to her first class, and meanwhile try to figure out what to do.
She remained hyper-aware of her condition, keeping her legs tightly closed until the class ended. Then she hurried through the halls in search of Alan.
She figured, Brother's the only one I can tell this problem to. And he HAS to find a solution, because I can't think of anything. What am I supposed to do - just ask a friend if I can wear her panties? No way, and no one would agree to that anyway!
She found Alan near the end of the break period. They quickly made plans to meet again in a quiet place after the end of the next class.
An hour later, she immediately ran up to him and said, "Brother, I've got a big problem! I forgot to wear panties today. And I have cheerleader practice for my last class today, and then we go cheer for our football game after school! What am I going to do?"
"Why did you forget something like that?" he asked.
"Never mind about that. There's no time!"
They quickly ruled out possibilities. The school had fences all around it, and no one was allowed to leave the school grounds at lunchtime. Even if one could escape, there was nowhere nearby to buy a pair of panties, as the school was in the middle of a residential area. Their talk had shifted to finding some way for her to fake being sick and leave school early, when they ran out of time. They both hurried back to their classes.
They resumed their discussion at the next break between classes.
Alan immediately said, "I've been thinking, and I have a crazy idea that just might allow you to attend the game. But it's really crazy. I'm sure you'll say no."
"What is it? I'm ready for anything."
"This sounds weird, but what if we painted a pair of panties on you? All the cheerleaders wear black undies. I swiped some brushes and quick-drying black paint from art class, so I could paint you during lunch if you want."
Katherine thought about it. She wasn't big on the idea, but it sounded like something really kinky that she could do with him. Brother would have to get really up close and personal with my naked pussy to do the painting, hee-hee. But what if I get caught? I'll be made a laughingstock!
"What about, you know, my hair down there?" she asked.
"Luckily, your hair is almost black, and the cheerleader underwear is black. And you keep it closely trimmed. That's why I was thinking it just might work. If worse comes to worst, we could shave that off. But you never know. I wouldn't worry about the game, 'cos you'll be at least fifty feet from the stands, and more like a hundred feet from where most people sit. It's the practice in your last class that you should worry about, particularly during your high kicks."
She couldn't resist a tease. She leaned against him and asked: "How do you know my hair down there is almost black? Have you been peeking?"
"It's pretty much the same color as the dark brown hair on your head, silly."
She teased some more, "Then how do you know that I keep it closely trimmed? It sounds like you're intimately familiar with the appearance of my pussy."
He tried his best to remain businesslike and ignore the teasing. "You've been flashing it enough lately! Anyway, if we do this, I'm going to have to get a lot more familiar with it, if I'm going to paint you. We have to be quick: do you want me to paint you or not?"
She quickly considered the plusses and minuses. Finally she said, "This could be the biggest mistake of my life, but I'll do it. Anything for you, Big Brother!"
"For me?" he asked quizzically. "I'm doing this to help YOU. In any case, meet me at the start of lunch in the north end of the hallway, upstairs. There's a supply closet we can use there. But hurry. We'll have to use every minute of lunch, and there'll be no time to eat, I'm afraid. If it doesn't work, or if someone starts to suspect, I'll just announce that you're sick, and help you get back home."
He ran to his next class, which was Ms. Rhymer's. Alan again gave her the impression of being distracted, but for once it wasn't because of sex - he was thinking about the logistics of the paint job and the odds of her going undetected.
— — —
Back at home, Susan started her daily task of looking for and collecting dirty laundry in her kids' bedrooms. Once she entered Alan's bedroom, she couldn't resist when she found the towel Alan had used to masturbate into that very morning, barely half an hour earlier. To her great delight, she discovered that the sperm was still a bit wet due to how the towel had been folded. Her resolve crumbled; she played with it with her fingers before sniffing and then tasting it.
What am I doing? This is so wrong, yet so delicious. Why can't I stop myself? I need to get a grip. Ron will be home soon. What would he think if he caught me doing this? I just can't allow this to go on.
With this new resolve, she quickly licked her fingers clean, then sucked some more out of the towel as a parting gift to herself. After changing the sheets and collecting the remainder of Alan's laundry, she moved on to Katherine's room, where she found that Katherine had already changed the sheets on her bed.
She sighed to herself and took everything to the laundry room. It seems I can't escape evidence on my son's virility. Even when he's not home, he leaves these spermy "gifts" that drive me crazy! I have to be on my best behavior, because Ron's in town. But what'll happen when he leaves?!
Again, she inhaled quickly the aroma of Alan's towel before putting it in the washer and heading upstairs for another "breast exam."
Both brother and sister ran breathlessly to the supply closet when the fourth period ended. Katherine ran with her hands on the front and back of her groin region, ensuring that her very short skirt didn't fly up as she ran, since her skirt only extended about two inches below her pussy.
They ducked into the supply closet as soon as the coast was clear.
Katherine immediately saw why Alan had chosen it. It was like a narrow hallway, and it had a door to a smaller, inner supply closet at the back.
They went into that room and turned on the light. There was so much stuff everywhere that there wasn't much room for two people, but they managed. They used the back room so that someone could still open the first door from the hallway and perhaps not realize that people were in the inner closet.
"Turn around, pull up your skirt, and pin it to your sides with your arms," said Alan in a commanding whisper. "You're going to have to stay in that position for a while."
He squatted only inches from his sister's butt. "We'll do the ass first, 'cos it should be easier. It'll be faster and less tiring if you kneel and bend over so you don't have to hold the skirt up."
Katherine got on all fours and bent down, with her head near the floor, allowing him not only to study her butt in great detail but also to examine every intimate nook and cranny of her pussy despite having only an overhead light source.
The sight took his breath away. In fact, the only pussy he'd been able to examine closely so far was Suzanne's, and even then he'd had limited access. Now he could take more time and even touch it as much as he wanted.
He leaned forward until his face was just inches from her ass. He inhaled deeply the scent of her ass and pussy. That made his erection strain so much against his shorts that it took all his willpower not to lean forward and lick her puckered anus.
Finally, he continued, "Here, show me with your hands exactly where the edges of your underpants go."
She reached behind and drew two lines with her hands. They were exactly the same as the tan lines from her bathing suit, which made his job easy.
Alan was actually amazed at just how revealing the cheerleader outfits were, considering that they were for high-school teenagers.
He immediately began painting and tried to imagine he was just painting a statue. He thought the task might take the whole lunch period, which would leave no time for it to dry. "This is a special fast-drying latex paint. You're lucky I'm taking art this semester so I have access to these supplies. Because it's latex, it won't damage your skin like an oil paint, and, like exterior house paint, once it dries it won't smear or come off if it gets wet with sweat or whatever."
"When I think about your face only inches from my butt, I'm afraid there might be a lot of leakage of 'whatever' before too long," Katherine giggled.
"Come on!" he urged. "Let's get serious here. There's no time to play around."
"Does that mean you'll play around with me later, when we have more time?" she teased.
He chided, "Don't tease or you'll leave here with just half a black butt!"
He sped on, but he was actually pleasantly surprised at how fast the painting went. Within three minutes, he had pretty much painted her whole ass. He mostly used a wide brush, but switched to a narrow brush for the edges.
"I'm almost done with the back," he proudly announced.
"I think you need to pay more attention to the crack," she said seductively. "And I would rather you stick something thicker in there than that skinny little stick you're using. I know just the thing, and you have it in your shorts," she giggled.
He laughed too, but was disturbed and nervous. Would she really want me to fuck her? Especially after Mom's new attitude? "Sis, I'm shocked! You never used to talk like that before."
"Well, I've never had my brother paint my butt before!"
They both laughed again. Despite himself, Alan found that he was getting over the morose feeling that he'd had that morning because of his recent tribulations with his mother.
"Shhhh! No more jokes; we have to keep it down. People use this closet sometimes, you know." He dropped his voice to a near whisper. "And also, since we're doing this in kind of a public place, it's probably prudent that you call me something other than 'Brother.'" His voice returned to its normal volume. "Okay, now we have to do the front."
"Oh goody, B.B.! The act we've all been waiting for!" she giggled. She'd never called him 'B.B.' before, which was obviously short for 'Big Brother', but that was the first thing to come to mind since he didn't want her to say anything that showed they were siblings.
"Come on, Kat; you're making this very hard." He didn't call her 'Kat' much except when Amy was there with them too, but he forced himself to use it now so he wouldn't say 'Sis' while engaging in such a compromising act in school.
"There are other parts of you I'd rather make hard. Maybe next time I can paint YOUR privates? I know what part I'd like to spend a long time on! Then afterwards we can test if the paint's dry enough by sticking it in a certain wet hole."
"Kat, do you realize what you're saying?! Do you really mean that?" He wasn't really sure what he wanted when it came to that. As much as he was attracted to her, she was his sister, so this was a huge, irreversible, step to take.
"Sorry, Bro. Er, I mean B.B. It's just that, especially since Mom and Aunt Suzy turned all fuddy-duddy, I thought a little teasing could do you a world of good."
He rolled his eyes, obviously annoyed at her use of terms like 'Mom'. He hoped his expression made clear that he didn't want her to use that word either. "Thanks, I guess, but we're losing precious time. I'll put the brushes down and hold up your skirt while you draw the cut of your panties in the front. You'll have to stand up for this part."
She quickly stood and indicated the area to be painted. It covered the entire V-shaped area between her legs and a little more than her tan lines.
He painted as fast as he could, going right to the edge of her bush. Again, he traced the outlines first with a small brush, and then quickly filled in the rest with a larger one.
"I may have to get a little paint on the edge of your bush," he said as he got near to finishing all but her most private region. He actually painted over her pubic hair along all the edges.
"That's okay; you can do anything with my bush that you like."
"Kat! Don't talk like that!"
"But it's so fun! It's just teasing."
"I think this new Kat is dangerous."
"I'm only like this with you."
"Dangerous for me then. In any case, I think I'm finished painting. Why don't you step back so I can see how it looks at a distance?"
She stepped back, and then whispered in a little girl's voice, "Oh no, old man, don't look at my cute little virgin pussy! The wind has blown my skirt up and I can't get it back down! Whatever will I do?"
"Very funny. Ha-ha." He tried to sound sarcastic and annoyed, but he still had a raging erection in his shorts. "Sorry, little girl, but I'm afraid there's one problem. It's possible to see your pussy lips. Especially if you get excited like you are now, your pink pussy lips will stand out from a mile away."
"Uh-oh," she said, now in her normal voice. "Does that mean the whole thing won't work?"
"Well, I could try painting them too, I guess, but I don't know if the paint will stay on."
"Oh goody!" she said again in her little girl's voice. "Now the dirty old man is going to touch my pussy!"
"Only with my paintbrush, you evil little girl. And before you start making lewd comments about my paintbrush and the size thereof, may I remind you that if you get wet down there I can't paint. So think and say nothing but wholesome thoughts. Better yet, don't say anything at all, 'cos I have the feeling that anything you say today is going to come out horny."
She giggled. "All right, I'll think completely wholesome thoughts about your dick. And wholesome thoughts about how you're going to stick it in my hole some."
Alan couldn't help but laugh at her 'hole some' pun, and laughed even more than usual to relieve his tension. But he said, "Okay, that's it. Don't talk at all, period. I'm serious."
Using the detail brush, he painted her labia. They actually were already fairly wet. He tried to dry them off as best he could with the back of his hand, and then painted some more.
Katherine, meanwhile, actually did her best to keep her mouth shut.
To his surprise, the paint stuck even there, on parts of her labia that were normally hidden from sight. It was really the perfect paint to use, he reflected.
"All right. You're lucky," he finally said. "This paint is so amazing, I could probably paint Jell-O with it. Now all we have to do is wait for it to dry."
"Thanks a lot, B.B. Can I talk now?"
"No! Not unless it's completely nonsexual."
"Then I have nothing to say," she teased.
Five minutes went by. Katherine continued to stand there with her skirt bunched up around her waist, completely exposing what was below. From a distance, now it really looked like she wore black panties. Alan had even drawn on the sides of her hips to imitate the little stretches of cloth which connected the front of her panties to the back.
The only jarring thing that really gave away the paint job was her pussy hair. Luckily, it was very closely trimmed. Without the hair, Alan was sure the paint job could fool anyone at a distance, given that the whole area was usually under a skirt, making it likely that she'd flash the crowd only briefly and occasionally. The only likely problem would be if someone nearby like the other cheerleaders got a good view from a few feet away.
Another five minutes went by. He'd finished the painting about ten minutes after the beginning of the lunch period, and the paint had dried for another ten minutes. Her skirt kept slipping lower, but it didn't really matter - he touched the paint and noticed that it was already almost dry.
They had another twenty minutes before the forty-minute lunch period was over. The paint job looked pretty good. The only problem was some lightness in the pussy-lip area and the fact that her bush stood out a bit. But overall it was hard to tell that anything was amiss.
He finally spoke up. "You know, if I'd known we had this much time, I would have tried to find some way to shave off all your pussy hair. Then it would be completely convincing."
"Don't worry," she replied. "We can do that next time."
"Next time? What are you talking about? There won't be a next time!"
"Don't get your panties in a bunch," she chided.
"If I had panties to get in a bunch, I'd give them to you-"
"And then we wouldn't have to do this." She finished his sentence. "I know."
"Hey, do you have a bag lunch in your backpack?" he asked.
"I do," she answered.
"We still have about twenty minutes to eat lunch, so why don't we share it?"
They did. He held up her skirt while she ate her half of a sandwich. They chatted about things at home.
"You know, B.B.," Katherine said, suddenly changing the subject, "This room is really perfect. Not just for painting people's privates, but for doing other things with those privates as well. I'm surprised people don't come in here to make out or have sex. Or do they?"
"They don't, 'cos you have to be a teacher's pet like me to be able to get a key to come in here in the first place. Didn't you notice that when I unlocked the door?"
"Who did you get it from? No, wait, let me guess. Ms. Rhymer."
"I have a really nasty thought."
"Those are the only thoughts you're having today!"
"Yeah, well, this is a really erotic experience. Do you know how sexy it is to imagine the hundreds of people in the stands today who will be looking at my completely naked pussy? At any time someone might realize I'm not wearing panties at all, and then they'll tell the next person, and soon the entire crowd will know. And then everyone will forget about the game, and stare only at me. Maybe they'll all decide that-"
"Whoa, whoa, there!" he interrupted. "Before you get too carried away in your slutty little fantasy, remember that the paint is still drying."
"All right, party-pooper. Anyway, it's good to keep the lips engorged a bit. Trust me, it's really erotic. I wonder how I'm going to stop from leaking like a broken faucet. Everyone will realize what's up when they see all the liquid pouring down my legs, and then I'll-"
"Time for a change of subject!" he interrupted again. "I'm afraid to ask, but what's this nasty thought of yours that you were going to say earlier?"
"Oh yeah, that. What if you don't return the key to Ms. Rhymer? Just say you forgot. I know a place that'll make a copy of any key, and then return it on Monday. And then you or I, or you AND I, could come in here anytime and do whatever we want!"
"I'm not even gonna go there and ask what we'd be doing in here," he said. "Don't you know how much trouble I could get in for doing that with the key? Especially with Ms. Rhymer. She'd never forgive me for breaking her trust, and I really like her; I don't want her mad at me."
"Well, if she's so mad at you, maybe she could take you in here and give you a proper spanking. Wouldn't you like that? And then when she's done spanking you, then I could think of some things she and I could do to your sore, red butt that would make it feel all better again," Katherine giggled.
"Kat. Really! Get a grip on reality. Anyways, it's not like that between her and me. I don't think of her that way. She's just a, uh, mentor-type figure."
"Yeah, right! I know what subject you'd like her to 'mentor' you in, and it isn't history. Come on; she's hot - even I might consider doing her. Everyone at home knows how you feel about her, so don't deny it."
He just had an "Aw, shucks," expression as he stared at his feet.
Changing the topic slightly, Katherine added, "You know what? This would be a great room for you to use with Christine as well. Lure her here on some nerdy pretext, and then whip out that impressive dick of yours and say, 'Worship THIS, baby!'"
"Sis, have you completely lost your mind? Do I look like the kind of guy who'd say 'Worship this, baby' in a million years? And if I did, the only question is which karate move she'd use on me first! Anyway, she's not interested in me at all."
Katherine kidded, "So you like the idea of doing the nasty with her in here; you just don't want to use that phrase?"
But he replied, "You're kinda freaking me out. It seems like you're thinking really, really unwholesome thoughts about me. You know about Mom's rules. That's just not right."
"Sorry, but you don't know how erotic this all is. I mean, you've been staring at my pussy for a good half hour now. I suppose you're just 'checking out the paint job.'" She said the latter part in a mock serious tone. She would have made quote marks in the air if her hands hadn't been holding up her skirt.
He didn't have anything to say to that, because he'd been busy checking out and memorizing every detail of her pussy the entire time.
Changing subjects, Katherine said, "This is even better than that day you rubbed all of our naked bodies with suntan lotion."
Alan didn't need to be reminded of that. It seemed like weeks had passed, but in fact it had only been four days since he'd applied lotion to the naked backsides of his mother, Suzanne, and his sister Katherine as they sat by the pool.
Alan was already extremely hard and horny, trapped in a tiny space with his even hornier sister. Thinking about the pool incident just made him even more frazzled. He was having very unwholesome thoughts about Katherine, even though he tried to deny that fact to himself. However, he couldn't resist asking, "Oh yeah. What happened after I left?"
"We all flipped over to our front sides, but unfortunately you had scampered away. Aunt Suzy had many more fun ideas to torture you with. But since you'd left, she told Mom and me in great detail what the two of you had just done, and how you reached orgasm in the pool just a few feet away from us. The three of us were completely wasted on alcohol by the time you came to the pool, by the way."
"I noticed that."
"Yeah. Well, we all sat there next to each other totally naked, and there was definitely some kind of lesbian buzz in the air, mostly radiating from Aunt Suzy. She definitely has a healthy sex drive!"
"I noticed that too." He chuckled while he fondly remembered some of the things he'd done with Suzanne recently.
"I know you have." Katherine wiggled her eyebrows suggestively. "You make me jealous just thinking about you and her together, and all the fun you two have been having."
Unexpectedly, he raised his hand, and said, "Hold on. I've been spacing out for a sec on this, but we really shouldn't use terms like ... you know." He dropped his voice, and whispered, "Mom. And Aunt Suzy."
Katherine rolled her eyes. "Oh, come on! Who's gonna know? No one can hear us here. Even having to call you 'B.B.' is silly."
"Maybe so, but just humor me, okay? Better safe than sorry."
She rolled her eyes, but also huffed, "Fine. Anyway, as soon as you left, we all wanted to frig ourselves really bad. Especially after hearing Aunt Suzy's story. Oops, sorry. I mean, the story from Our Neighbor With The Great Gazongas. Or, as I like to call her, O.N.W.T.G.G." She giggled.
Now it was Alan's turn to roll his eyes.
She continued, "But we were still too shy to do it with the other two there. Or at least I was. I doubt at least if Aunt Suzy cared. Er, I mean A.S. How's that for a name?"
She continued, "But then A.S. suggested that we could use the pool just like you did. So M. jumped in and quickly brought herself off. You know who I mean by 'M.' right?" Katherine held her hands out in front of her chest, greatly exaggerating the size of their mother's boobs.
"Of course!" he said with a smile.
"Okay. M. was desperate for relief by that point. Then she got out, and I did the same. I stood right where you had stood to do it not long before. By the time I got back, A.S. had already gotten herself off just sitting on the lounge chair. M. probably watched that from close up, but I'm not sure. You couldn't miss the puddle of cum A.S. left on her chair, though."
She went on, "But getting ourselves off didn't seem to cool us down at all. I think a lot of it had to do with being naked outside for the first time. You know, the thrill that anyone could be watching, and us checking each other out too. We were so fucking hot, all of us. Squirming around in our chairs. Putting on more lotion constantly, mostly rubbing it on our breasts and pussies. A.S. kept suggesting that you'd go to the window of my room to spy on us, and we all kept looking up to my bedroom window, half expecting to see you. But you never spied on us, you dummy."
He answered, "No, I honestly didn't. I masturbated and then fell asleep. I hate getting so tired and having to take a nap every day, but I can't help it."
Katherine continued, "That's why you need our help with your cock. That's why you have to have your sister lick it for you and make it all better. Aren't we all so lucky you have that problem?"
She made a move towards him, but he said, "Hey! Remember about keeping it cool?"
She stuck her tongue out at him with a pout and continued, "Anyway, I remember lying there by the side of the pool with my feet dangling in the water. A.S. stood up and looked at me in a really sultry way. We were all so horny, so fucking out-of-control horny."
She fanned herself, as if overcome by sexual heat. "Speaking for myself, I was ready to fuck a rock, a carrot, an elephant - anything! So A.S. was looking pretty good. She asked me if I needed more suntan lotion. I could tell she wanted to put it all over me, even though M. was sitting right there. But I told her 'No'; I got a little scared. Things broke up not long after that. And then we all left and diddled ourselves even more in private. At least, I know I did!"
She sighed in fond remembrance. "I'll tell you, the whole thing was about the hottest, sexiest experience I've ever had. Especially when you were still there and putting lotion on me. If you had come back later, we would have all been lining up, on our hands and knees, our naked asses wiggling with desperation, begging to be the one who got to be fucked first!"
He dismissed the idea. "Like that'll ever happen. You're exaggerating, just like the comment about the elephant." To himself he thought, There's a mental image I'm not going to be able to get out of my head for a while!
"Maybe, B.B. Maybe. Or maybe it was just the heat of the moment. Or the alcohol. I think Mom actually got ill later. You know how alcohol affects her so easily. In any case, if you had come back down it would have been a load of fun, I guarantee you that... You don't think A.S. has lesbian tendencies, do you?"
"Of course not. I can attest first-hand that she very much likes men."
"I'll bet you can!" Katherine giggled. "But I mean, you know, being bisexual."
"She was probably just carried away by the situation, like straight guys being temporarily gay in prison."
"Yeah, I guess that's it," Katherine said, but she wasn't so sure.
"Um, Kat, maybe this isn't the best time to ask this, but you said something earlier in your little girl's voice about your 'little virgin pussy.' Was that just playing, or are you still a virgin?"
"Thanks for asking about my pussy! I'd be happy to tell you all about it, any time!" she giggled some more. "Honestly, whenever I get serious with some guy, Mom yanks my chain and makes me dump him. Oops! I mean M. does. Do we really have to continue with these silly nicknames?"
"Fine. Sheesh. The point is, they're never good enough for her little angel. So I'm still a virgin. That's okay though, 'cos I'm trying to save myself for my B.B."
That was partially the truth. In reality, she hadn't done much with other guys because of her lust for her brother, and the only reason she'd dated other guys at all was because she thought her feelings for him were completely unrealistic and she was trying to "cure" herself of them. But then everything had changed.
"Kat, you can't talk that way! It's really disturbing me. Teasing is one thing. Remember the limits! I'll just chalk it down to you getting too excited because of the whole paint job."
"You do that. It's just teasing, anyway. And my hymen broke when I was a kid, so you won't have to worry about the blood when you push your big, thick cock in my tiny, tight, ready and waiting pussy. I'm sure that must be why you asked."
"Kat! What if someone heard you talking?" She wasn't far off on why he was curious, but he still fiercely resisted crossing over from fantasy into reality.
"You know I'm not really serious, 'cos that would be wrong, wouldn't it? Or am I serious? Wouldn't you like to know!" She laughed again.
All of a sudden, Alan thought about the time. "Oh my God! What time is it? I'll bet the lunch period will be over in only a few minutes. Let's check to see if you're dry by now."
Ever since he'd stopped painting, both Alan and Katherine had been standing, so he couldn't really look at her exposed privates, especially since he had tried desperately to maintain eye contact. But after they both released her skirt, letting it fall, he got down on his knees behind her and put his head under her skirt. The nominal idea was that this would allow him to see and touch the paint job, but he really just wanted to get his nose back to within inches of his sister's pussy.
It was actually too dark to see that way, but he didn't care. He ran his hands over her butt, ostensibly to check whether the paint was dry. It was, but he checked it for another minute or so, "just to be sure." He then pried open her outer labia with his fingers, and took an even longer time determining that the paint was dry even there. He deeply inhaled the smell of Katherine's nether regions, and liked it.
He was considering putting his nose straight into her gash when Katherine finally spoke, playfully suggesting, "You know, if you really want to make sure the paint is dry, it might be more accurate to check with your tongue."
"Ha-ha, Kat," he said humorlessly, even though he was thinking the same thing. He felt things were going too fast though, and was trying not to encourage her. "You really are too much to take; do you know that?"
"I know. But seriously, I want to be able to help you too. You know, what M. and A.S. are doing. Rubbing your dick. I'm happy to help, too. I want to hold your dick, too. And rub it. And suck it, even! Why haven't you asked me to help you in that way yet? I've been waiting for it, eagerly! I'm completely serious this time. You can't say it's 'cos I'm your you-know-what, 'cos M. has been helping you too. But now that she's gone all moral, it should be my turn to take over."
Alan motioned for Katherine to turn around, and she did. He felt all over the front of her crotch. He even ran his hands through her pubic hair, even though there was no paint there. The only reason he did it was because her talk made him so hot.
"She has, hasn't she?" he asked, to buy time.
"Yeah. I'm not too surprised. There really must be an intense battle raging inside her. Not with me, though; I'm soooo ready to help out! So how 'bout it?"
After thinking for a while of a suitable response to her suggestion, he finally said, "Um, I'm certainly wowed by that offer, but now's not the time to talk about that. We've got to run to class." He was very conflicted about the idea, and didn't know what he really wanted.
"All right," Katherine sighed. "God, I want to suck it, though." Her whole body started to shake mere inches from Alan's nose in response to the movement of his hands.
She continued, "But tell me one thing. Is it that you don't find me attractive? I know I'm not a bombshell like those two-"
"Sis, you are too a bombshell! I find you extremely attractive." He spoke directly into her pussy. "That's the problem. God, you're so hot! You're centerfold material. Seriously. But you're eager. TOO eager. That's the bigger problem. Where would it all lead?"
Alan ran his hands over her pussy lips in a most un-brotherly manner, and "accidentally" tweaked her clit. But realizing the bell for class would ring in a minute or two, he used all of his remaining willpower to stand up and take his hands off his sister. "See? Look. I can hardly control myself, and you're not telling me to stop like you should."
"Why should you stop, or we stop, when it feels so good?"
He ignored the question and instead suggested, "Try not to move around when you sit. Now, let's get out of here! Remember that little thing called class?" He swatted her on the butt playfully.
There were two class periods after lunch. Katherine's paint job dried completely during the fifth period. Sixth period was her cheerleader practice. Since the cheerleaders had a football game to cheer at immediately afterwards, they had only a light practice of stretches and warm-ups, and a review of what they would be doing later during the game. They practiced on a little-used lawn that was separated from the football field by only a chain-link fence. The football players could see them from about 100 yards away while they too were warming up for the game.
Katherine was almost certain that no one would notice her paint job. In fact, it was so convincing that she made it through most of her cheerleader practice before there was any trouble.
The head cheerleader's name was Heather. She was gorgeous. She lived the clichéd life of going out with the star quarterback on the football team, and she was a near-certain lock for both Homecoming Queen and the Most Popular award later in the year.
She had long blonde hair that she usually wore in a ponytail, pouty red lips, shining eyes, and a deeply tanned, tall body. It was rare for someone so blonde to be so tanned, but she worked at it. It was rumored that even her most private places were just as tanned as the rest of her, and that was true. But it was her big breasts and perfect facial features which won her fame at school (even though it was widely believed that her breasts were largely implants).
Inwardly, she actually was an immoral, stuck-up, horny bitch who cheated on her boyfriend all the time. She was demanding and domineering with everyone. Her haughtiness, however, seemed only to make her more popular and unobtainable.
There were six cheerleaders on the varsity squad: Heather, Katherine, Amy and three others named Kim, Janice and Joy. Because of budget cuts and the resultant teacher shortage, plus Heather's previous years of experience and some kind of mysterious power play she had pulled, there wasn't any teacher monitoring them. As a result, Heather had complete control over the squad. Behind her back, the others not-so-jokingly called her "Little Hitler" for the way she ran the squad. More commonly, they just called her "bitch."
Heather faced the other five as she led the exercises, so only she was in a position to closely observe them. With the class period nearing its end, she finally noticed something odd about Katherine - something about the way that she was protecting her body - but Heather couldn't put her finger on it. Suspicious, she ordered them all to do a variety of warm-up exercises.
She found out why Katherine was acting strangely during one stretching exercise where they each pulled one of their legs all the way up to their heads as they stood.
Heather walked over to her. One of Katherine's legs pointed straight up towards the sky. She put her hand on Katherine's butt, under the skirt, as if to help her stretch even higher.
Heather's hand slid up a bit, and then she felt the lack of any underwear. Whoa! What do we have here? she thought. It's just as I thought, but I can't believe it!
"Katherine, are you having trouble with your stretch?" With her other hand Heather reached straight for Katherine's slit, and stuck a finger inside it.
Katherine silently gasped. "Um, n-no! I-I-I'm good!" she stammered.
"I don't know," said Heather. "You feel really ... tight." She stuck a second finger into Katherine's slit as she said that.
Although Heather favored sex with men, she was actually bisexual. She'd already figured out ways to demand sex with Kim, Janice, and Joy, all of whom strongly disliked her as a result. So far, she hadn't demanded sex with either Katherine or Amy, because they were both believed to be completely straight virgins, which made Heather extra cautious.
But finding Katherine with painted-on panties instead of real ones made Heather completely reassess that 'known fact'. She figured that Katherine's condition made her fair game, and she certainly was aroused by Katherine's great beauty. She wiggled her two fingers deeper into Katherine's slit.
Katherine gasped in horror. To any distant outside observer, it looked like Heather was merely trying to hold her up with both hands to prevent her from falling.
"I think it's good if you loosen up," Heather suggested with a smirk. "I think you may have a strained muscle or something." She plowed her two fingers in and out of Katherine's slit as discretely as she could manage, since the other cheerleaders stood exercising just a few feet away. Heather was not only very active sexually, but she also loved the thrill of danger.
"Um, whatever you say," said Katherine. She was petrified. She looked over towards the other cheerleaders, and luckily they continued their exercises, oblivious. But Katherine knew that, with a few words to alert them, the bitchy Heather could now destroy her completely. She was totally at Heather's mercy.
Heather wanted to have more fun with Katherine, but she knew she couldn't at that moment because all the other cheerleaders were waiting for her, especially since it was game day. If she were to delay any longer, they would start to look closely at her hold on Katherine, and the gig would be up.
So she thought: How can I take advantage of this? If I can't enjoy this right now, then I'll hand Katherine over to someone who can, and then join in the fun later.
She walked back in front of the group and looked over the other cheerleaders. What about Kim? She's a total lesbian, I know that. She'll definitely like this, and will owe me one.
"Kim," said Heather, "I'm worried about Kathy here." Katherine hated that nickname, which only Heather was insensitive and cruel enough to use. "I think she's got a muscle cramp coming on, but doesn't want to admit it. Can you take her over there" - she pointed to a spot on the lawn about ten yards away - "and help her get limbered up? I think the cramp is right in the front groin area, so don't miss that."
Kim had medium-length, brown hair, and was the shortest person on the team. She was about as beautiful as everyone else on the cheerleading squad, who all looked like stereotypically-gorgeous Southern California cheerleaders. She was also the youngest on the squad in both appearance and maturity level, and she was still growing into her body. She, Amy, and Katherine were the new members of this year's cheerleading squad.
Heather smiled like a shark that had just found its next meal. She'd picked a spot in the opposite direction from where all the other cheerleaders faced. That way, she could see what Kim was doing while she continued to lead the practice, but the other cheerleaders couldn't. But there was always the possibility any of them might turn around, especially if she stared in that direction too much.
At the last second, Heather whispered in Kim's ear, "Give her the finger, if you know what I mean!"
Kim had no idea what that meant. Her first guess was that she meant giving the middle finger sign, and that didn't make any sense. But she didn't want to cross Heather, who hated to suffer fools, so she pretended like she understood. She hoped something would happen to help explain the cryptic comment.
Kim and Katherine walked away from the others.
The two of them walked to the spot that Heather had indicated, and then stopped.
Katherine's heart was beating in fear like a loud drum. Between traffic noise and the general noise of being outdoors, they were pretty much out of earshot of the other cheerleaders, unless one of them said something loud.
"All righty, let's see what the problem is," said Kim. She flipped up the front of Katherine's skirt, intending to apply a bit of massage. The black paint job and black-haired pussy stared back at her and she suddenly realized Heather's real meaning.
"Oh my!" was all Kim could say.
"Please have mercy!" whispered Katherine frantically. "Just don't tell anyone! It was an accident!"
Kim's facial expression changed as she suddenly realized the position of power she suddenly found herself in. Like Heather, Kim assumed that Katherine had to have a majorly kinky side to be practicing with painted-on panties, especially on a game day. And, like Heather, she took that to mean that Katherine was fair game for almost any kind of sexual fun.
Katherine trembled in fear. It was one thing to tease her brother, whom she loved dearly. It was another thing altogether to be at the mercy of someone she disliked, like Heather, or didn't know well, like Kim. The two of them hadn't really known each other at all until cheerleading practice began a few weeks before.
Kim put a finger into Katherine's already very wet cunt, and noted that Katherine didn't say or do anything about it. So she began pistoning in and out with her finger.
"An accident, huh?" Kim finally said after a minute or so passed. "Somehow you just accidentally got painted-on underwear? How does that happen by accident?"
"It's a long story. Are you going to tell anyone? Please don't tell anyone!" Katherine pleaded.
"Well, that depends. Are you going to cooperate?"
"Yes. Yes. Anything!"
"Goody! Anything? So you don't mind if I do this?" She took three fingers and stuffed them all in Katherine's cunt.
Katherine gasped at the massive intrusion, but didn't say anything. She didn't want to attract any more attention. It was bad enough that Heather was constantly looking over in their direction.
Kim prodded, "I asked you a question. Do you mind?"
"N-n-no. I don't mind." Katherine shuddered in both fear and horniness.
"Cool. Let's get down on the ground and make it look like we're stretching. Let's sit just the right distance apart so we're one arm's length from each other when we're all stretched out. Then I'll reach over and put my hands on your pussy, but it'll look like I'm doing a full stretch. Then you'll reach over and put your fingers in my cunt. Think you can handle that?"
"Yes," Katherine said weakly.
They both got into position, completely spread-eagled on the ground. From a distance it looked like they were sitting across from each other and imitating the other's movements, each pulling their heads to the ground as they stretched. But if one were nearer and looked closely, one could notice that each woman had a hand under the skirt of the other.
Katherine pulled the thin band of cloth away from Kim's vulva, and stuck her fingers into another woman for the first time. She tried not to think about what she was doing, just operating on auto-pilot until the ordeal was over.
After a few minutes of this, curiosity got the best of Kim, and she quietly asked, "Okay, I'm dying to know: just why ARE your panties painted on? I thought you were the prudish one in our group, but you turn out to be secretly this totally kinky freakazoid!"
Katherine whispered back, "It's not like that! It was an accident!"
However, much to Katherine's consternation, she was forced to cut off her explanation. The other cheerleaders took a short break, during which Janice came over to see how Katherine was doing. Her curiosity was piqued because she noticed the other two were speaking in unusually hushed tones.
Kim immediately removed her hands from anywhere near Katherine's pussy, but still Katherine was deathly afraid that Janice would notice the paint job.
Even Kim was terribly nervous. She put up a tough front, but her bravado hid her butterflies.
"How's it coming, Katherine? Muscle cramp, huh?" Janice knelt right behind Katherine and even put her hands on her shoulders.
"Need any help? I'd be happy to massage your thigh muscles."
"No thanks!" Katherine said far too loudly. "Um, I'm cool. Kim is helping out."
Janice walked off after another few moments of chitchat. She was still a bit curious about all the whispering, but she had other things to do.
Kim immediately had both of them get back into position, fingers in each other's pussies. "Let's just stay like this for a while," she said. "I don't know how we're gonna do it, but we're not gonna leave here until you get me off."
"Will you be quiet then?" Katherine asked.
"If you do all I say, I will. But I'm not through with you yet! I had no idea you were like this. You seemed like such a prude, to be frank. ... Tell me, are you seriously planning to go to the football game like that?"
"I didn't plan it, exactly. Like I said, this was an accident! I AM prudish. I forgot to wear panties this morning, and so this was an emergency solution. I got painted during lunch. It was either that, or wear nothing at all!"
"Good Lord, girl, I thought you were the most frigid of us cheerleaders, and it turns out you were the hottest of us all. That takes some wicked serious guts! And if you're prudish, you finger a pussy pretty well for a prude."
Katherine had no reply to that.
They both continued to plunge their fingers into each other's pussies as they talked. They bobbed their bodies to make it look like they were stretching, which caused their fingers to piston in and out.
After a while, Katherine asked, "Kim, I know you're a lesbian, but why do you assume that I'll enjoy fingering you too?"
"Well, do you?"
Katherine thought about it. She was surprised to find that she was starting to actually enjoy the fingering. It was just like masturbation, except better because you never knew what the other's fingers were going to do. Had it not been for the unfortunate circumstances, she would have liked it a lot more. She kind of dodged the question by saying, "I don't like the fact that you're forcing me to do it. I thought you were a nice person!"
Kim grimaced. She was a nice person, normally. However, the situation had made her lose control a little bit. Plus, she explained, "Look. We HAVE to do this. You know what Heather whispered in my ear, just before she walked away?"
"What?" Katherine did remember seeing the whispering.
"She told me to give you the finger. I think her exact words were, 'Give her the finger, if you know what I mean.' At first, I didn't understand, but once I saw your painted panties, her meaning was obvious. Especially since she gave me, the one open lesbian in the squad, the task. You think I want to disobey Heather and get on her shit list? No thanks!"
Katherine didn't know how to respond to that, since she greatly feared Heather as well. But her silence showed she understood the pressure Kim was under.
"Who painted you?" asked Kim after a while.
"Pardon me?" Her nervous jitters came back instantly.
"You heard me. Who painted you? Don't tell me you painted yourself. Tell me the truth, or I might just show your paint job to the other cheerleaders and get their opinion on who did it."
"Promise not to tell anyone who it is?"
"You're not in a position to be asking favors. Yeah, I promise, but that means you'll owe me one. Which you already do. You'll have to pleasure me again and more extensively on some other day. Which is something you already have to do, so I guess it doesn't matter. I'll have to consult with Heather and figure out just what kind of fun we're going to have with you."
"I'm so ashamed! He would kill me for telling. It was my brother, Alan."
"Your brother? Kinky! God, even your puffed-up pussy lips are painted thoroughly, and by your brother!"
Katherine immediately realized it was stupid to have made that confession, but it was too late to take it back. She tried to minimize the implications. "It's not like that! It was a practical thing. Who else could I ask to do that favor? It's not like I was going to ask a stranger! I figured that, with my brother, he'd respect, you know, my chastity. He was a total gentleman about it."
"Not a bad choice. Your brother is pretty cute. All right, that gives me an idea. I think I have a plan on how we can punish you properly. Let's see if your little paint job works in the game, and meanwhile I'll talk it over with Heather. But for now, let's switch positions so you can finger me better. I wish I could just rub my hands all over your sweet black butt and your magnificent tits. But that will have to wait for another time."
Katherine's tits were quite a bit bigger than Kim's, and the lesbian cheerleader had fantasized about touching them ever since she'd joined the team. In fact, she had fantasies involving all the other cheerleaders, since she was a lesbian and they were all gorgeous. She even fantasized about Heather: she hated her personality, but loved her body.
Katherine literally trembled in anticipation. She knew she liked guys (and especially Alan!) too much to be a lesbian, but she had to admit that being fingered briefly by Heather and then more extensively by Kim really got her hot. The feeling of stretching her pussy over the fresh green grass while Kim's lithe little fingers played around inside her cunt in direct sight of the knowing Heather and within possible sight of the other cheerleaders and even of the football players was nearly too much for her.
In the fifteen or so minutes that Kim and Katherine had fingered each other on the lawn, their cover as stretching exercises had become increasingly less plausible.
Kim had even considered ordering Katherine to lick her, but couldn't think of a remotely plausible cover exercise for that, and especially worried about drawing the attention of the football players.
Meanwhile, Heather had to go out of her way to avoid any exercises which involved the cheerleaders turning around, or everything would have been exposed instantly. Kim and Katherine each climaxed over and over, though they were very careful to be completely quiet about it.
When practice ended, Katherine had to ask Kim to take a close look at her paint job, to make sure all the frigging and leaking hadn't ruined it.
Kim gladly did so. She lay on the ground and looked up between Katherine's legs as Katherine "accidentally" walked over her. She gave Katherine the bad news that, unfortunately, the pink parts of her pussy lips, now engorged, were fairly visible. That just made both of them hotter, because it was clearly too late for Katherine to turn back from cheerleading just because she was without panties.
Alan, meanwhile, was at the game to look out for his sister (and to look at her too). Because he got there early, he went down to the field to say "Hi" to Katherine and Amy.
When he did so, Katherine and Kim were standing together. He noticed there was something odd about them, but he couldn't quite understand it. They seemed strangely energized, with both of them staring at him very intently. He knew Katherine was wearing nothing but painted-on panties underneath, so he could understand her behavior a bit, but he didn't get why Kim seemed to be acting the exact same way.
But after he said his hellos, Kim took him aside and spoke to him for a minute or two. He found that odd as well, because it seemed that she wanted to tell him something important, but she never quite did.
With more of the crowd showing up, Alan had to leave the field and go to the stands. He had borrowed a pair of binoculars, and then sat in the front row of the stands to get the closest view of his sister that he could. He also made a point of avoiding his friends so he could sit by himself, completely away from everyone else. Luckily, the stands were only half-filled and few wanted to sit in the front row, since the higher seats gave a better view of the game.
He told himself that he was merely interested in making sure the paint job worked well. However, he already had a stiff erection just from anticipating what he would see.
The game began, and the cheerleaders started to do their thing.
Alan couldn't see much of Katherine's privates with his naked eye. He didn't get many chances, because Katherine jumped around as little as possible. When he did get a chance, he thought he could see a flash of pink, and realized with a twinge in his dick that he must be seeing her labia.
But he wondered, Did I notice it only because I'm looking for it? Is it my imagination? Can others see it too?
However, it wasn't just in his mind. With the high-powered binoculars he had borrowed, everything was clear as day. Instead of being fifty or more feet away, it seemed to him like he was only five feet from her - he felt he could reach out and touch the clearly visible hairy mound of her pussy.
He quickly stopped and looked around at the crowd to see if anyone else had binoculars. Luckily, it was just an ordinary game between two high school teams, and no one else seemed to have cared enough to bring any. The crowd was pretty small in any case. He felt relieved, and went back to staring at his sister.
Down on the field, Kim stood next to Katherine as they jumped about. Heather was on Katherine's other side.
Kim whispered to Katherine, "I can see where your brother is in the stands."
"Where?" Katherine asked excitedly.
"There," Kim pointed. "He's in the very first row. And it looks like he has some serious binoculars and isn't pointing them at the game. Is that what you call 'brotherly love?'"
"I told you already it's not like that," said Katherine resentfully. She was seriously regretting having told Kim who'd painted her privates. She had a sinking feeling in her stomach that her incestuous situation was being exposed, and she didn't see what she could do to stop it.
But knowing that her brother was watching, and with binoculars to boot, she began to jump around more enthusiastically. It made her hot to think that, in fact, three other people already knew she wore no panties: Alan, Kim, and Heather.
— — —
Back in the stands, Alan's reverie was broken when he heard the voice of Christine behind him. "Hi Alan. What'cha looking at?"
Startled, he turned to face her guiltily. "Oh hi, Christine. What are you doing here?"
He said that relatively calmly, but inside he was panicking. Christine, of all people! Oh shit! We haven't really hung out in a significant way in a week. Why now, of all times? I feel too embarrassed to talk to her now.
Christine was still nervous about being with Alan after how she'd turned him down, but she was making a conscious effort to repair their friendship. Everyone thought she was as strong as steel, but she lacked a lot of confidence about certain things, most of them having to do with sex and relationships. She smiled and tried to act casual. "I just saw you here and thought I'd sit with you. What are you doing here? I thought you didn't like football, other than watching the Chargers."
Alan realized that it was clear he was looking at the cheerleaders and not the game. "I was ... looking at my sister doing her cheerleading. She asked me to watch. They've got a whole bunch of new moves, and she wanted to get my opinion about them."
"Oh really? Can I take a look?" Christine asked, even as she reached for the binoculars.
"No!" He lied, "Um, I mean, these binoculars are not mine. The guy I borrowed them from gave them to me very reluctantly. He said I could only use them if I didn't let anyone else touch them. So I really have to respect that."
"Okay. Geez. Not a big deal."
Phew! That was a close one. God, what if she saw me staring at my sister's pussy, flashing in the sun? She'd think I'm a total pervert, or worse. She'd never speak to me again!
Trying to distract her, he told one of the blonde jokes he'd saved up for his encounters with her. He liked telling Christine dumb-blonde jokes, mainly because she was blonde yet also the smartest person he knew, so he could tease her about being a "dumb blonde" in good fun. "Hey, Christine. What do you see when you look directly into a blonde's eyes?"
She rolled her eyes. "I don't know. What?"
"The back of her head."
"Ugh," Christine said while frowning, even though she found it amusing. She immediately shot back, "Okay, you and your 'dumb blonde' jokes, I've got a 'dumb teenage brunette boy named Alan' joke. You want to hear it?"
"How can you tell a fax has been sent from a dumb teenage brunette boy named Alan?"
He shrugged, since he didn't have a good answer.
"There's a stamp on it."
Alan smiled and said, "Harsh." Then, after a perfectly timed pause, he asked cluelessly, "Um, what's a stamp, exactly?"
Christine burst into laughter.
While they were joking around, Christine was generally looking towards the playing field, giving him a golden opportunity to ogle her. Peeking at her was a bit risky due to the intense disapproving glares he would get when she caught him doing so. As usual, she wore clothes that fully concealed her cleavage, along with jeans or pants that hid her legs. Even so, her body was so amazingly curvy that everyone considered her smoking hot.
Alan already had a raging hard-on from watching the cheerleaders, and now with Christine next to him he was having even more lewd thoughts. He realized that he needed to get away from this situation and cool down.
After some more idle conversation and joking around, he said out of the blue, "Actually, Christine, I think I've seen enough of the game. It's almost the end of the first half, and the cheerleaders just do the same stuff over and over after a while. Since neither of us really is into football and this game is pretty boring, why don't we go get some ice cream?"
She stood up to go. "That sounds great."
He said, "Here's a joke for you. A blonde female police officer pulls over a blonde gal for speeding. She walks up to the car and asks the blonde for her driver's license. She has to explain, 'It's that thing with your picture on it.' The blonde driver looks all over and finally pulls out her compact, opens it up, looks at herself, and then hands it to the cop."
He paused for effect, then went on, "The blonde cop looks at the compact, rolls her eyes, hands the compact back, and says, 'If you'd told me you were a police officer when I first pulled you over, we could have avoided this whole thing!'"
Christine laughed heartily.
Alan naturally enjoyed making people laugh, but he especially liked making Christine laugh because when she did she tended to close her eyes, giving him more opportunity to ogle her body. Laughing also usually caused her full breasts to jiggle in very delightful ways.
As he gawked, he thought, Dang! Massive jiggling on a Wonder Woman day, no less. And I'll bet she doesn't realize how much her chest thrusts forward when she puts her hands behind her back like that. Is there some kind of cosmic conspiracy to make me cum in my shorts today?
He was referring to the fact that she was wearing her Wonder Woman T-shirt. It was practically the only T-shirt that she owned - she normally wore blouses - and it was a bit tight on her. It showed off her chest more than anything else she wore. On a good day like today, he could even see a hint of nipple and the outlines of her bra straps. He loved what he called "Wonder Woman days" - the rare times she wore that shirt.
Christine finally opened her eyes. "You're so bad, Alan." But she couldn't stop smiling. Being with Alan always made her feel good.
Down on the field, Katherine saw Alan start to walk off with Christine. She had been jumping even more enthusiastically ever since she had seen Alan watching. She began to flash her pussy and her ass to the crowd more and more in an attempt to keep him from leaving, to no avail.
As soon as her brother left, her behavior changed again and she hardly moved at all. She was jealous of Christine. I thought she wasn't interested in him and he'd given up on her. And now they're going off together somewhere. Shit.
— — —
When half-time began, Kim came up to Katherine, grabbed her by the arm, and whispered in her ear, "I think I know one cheerleader who has very unnatural feelings for her brother! The evidence keeps piling up. I saw how you were putting on a show for him, and then stopped and got all bummed out. You can't deny it. I think Heather will find that most interesting!"
Katherine realized that she'd been busted. "No! You can't tell!" she whispered back.
"For such a smart girl, you're not very bright. You just confirmed it! To think that until today I thought you were so conservative! Okay, I'll keep it a secret, including from Heather, but now you REALLY owe me. In fact, I think that basically, you're my bitch. You're my slave. What do you think about that?"
"What are you going to make me do?" Katherine asked in fright. She had images of being tied up with ropes in a dungeon.
"Nothing too much, and I'm sure you'll enjoy yourself thoroughly, if today on the grass was any indication. For starters, I want you to wear the same painted-on panties to cheerleader practice all next week."
"That's the idea that Heather and I came up with. That's your punishment from her. But to get even with me, there's more. I want to wear the same thing next week too. I think it's totally hot. I'm waaaaay jealous! I wish I was you right now, flashing my cunny to hundreds of strangers! So you'll get your brother to paint me up too. How do you two do it, anyway?"
"He painted me during lunch, in a supply closet." Katherine was in a state of shock.
"Perfect. Sounds delicious. On top of that, any time I want your body, you come running. What are you doing tonight?"
"I have a date," she lied.
"With your brother, I'm sure," Kim snickered.
"No! That's not true!"
"Whatever. I want you to cancel it. You're cumming with me. Spelled C U M. You'll find I'm really not mean, and I'm not into anything weird. I just like to get off."
"I-I-I can't! My father is coming home, and he's been away for months! I'm going to be really busy this weekend!"
Kim remembered that Katherine had in fact previously mentioned her father coming home over the weekend, so she figured it wasn't a lie. "I'm sure we'll find some time. Starting after the game. Give me your phone number."
— — —
When the game ended, Heather and Kim took Katherine to a nearby supply shed and made her put her fingers in each of their pussies at the same time.
Katherine frigged first one and then the other and then back again. The whole time they talked to her in greater detail about her new, submissive situation.
Katherine protested that she had to leave immediately because her mother was coming to pick her up.
But they didn't let her off that easily. Heather, naturally in charge, said, "Katherine, since you're in such a rush we'll let you go, just as soon as you lick my pussy. Kim, you'll be getting plenty of this treatment from her in days to come, so be patient."
Kim just stayed silent and watched intently to see what Katherine would do.
Katherine pushed aside Heather's panties yet again. She noticed that the two girls seemed to mock her lack of panties by keeping their own on.
As she stared at Heather's pussy, she thought to herself, This morning I'd never even imagined touching a woman, and now I've already gotten intimate with two pussies at the same time! How crazy is that? To Heather, she said, "Look, later, but right now-"
"Stuff it," Heather interrupted. "If you argue, I'll make you spend more time arguing than just doing it, and in the end I'm going to make you do it anyway. Just give me a few licks to show me you're capable and understand your position. If you're really in a hurry, you'll just get it over with."
Katherine could see no way out. She looked intently at Heather's pussy. She had to admit that it was a really pretty one with nicely-formed lips and a cute little clit that poked out just below a furry patch of blonde pubic hair.
She bent down and gave a few perfunctory licks. She was surprised by the taste and smell, both of which she found very arousing. She found herself thinking she might get off on having her tongue slide into Heather's snatch, if it weren't for the humiliation she'd been put through.
Mercifully, Heather let her go after that, knowing that she'd have more opportunity with her later.
Katherine felt extremely weirded-out and humiliated by the whole episode and was grateful for it to be over.
If pressed, Katherine would have had to admit that theoretically she didn't terribly mind the idea of pleasuring or being pleasured by beautiful girls, and these were the most beautiful girls in the school, but she adamantly didn't want to be anyone's slave. She figured that situation could only go from bad to much worse, especially if Heather was involved.
So as soon as she got home, she told Alan everything that had happened, hoping he could help get her out of this mess. She just left out one little detail. She mentioned the part about how Kim claimed that she had a thing for Alan because of all that happened with the painting and binoculars, but she left out her admission that it was true. She was so concerned about all these problems that she didn't even try to tease or flirt with him as she told her story, although the details created a perfect opportunity.
When she was done, Alan suggested, "First, keep stalling for time. Kim has too many plans for you down the line to actually rat you out at this point if you don't see her this weekend. Just stall as much as you can."
"Meanwhile, I'm thinking the only way to get out of blackmail is counter-blackmail. We have to get Kim in some compromising situation so that she has to be the one to cry uncle. When that happens, her power over you will end immediately. We may have to do something with Heather too, but she's a tough one, if there's anything at all to the rumors of her bitchy reputation."
"There is, believe me, there is," Katherine frowned.
"That sucks," he said. "However, with Kim out of the picture it will be your word against Heather's, which is infinitely better than two against one. Since Kim is so set on doing this painted-underwear thing, we should have a lot of chances to get back at her. I'm thinking on game day next Friday, I switch the paint that I paint her with to something very water-soluble. Then all we have to do is threaten to get her wet, like splash some water on her in the middle of the game, and she'll be totally ruined! She'll have to agree to anything we say."
"Big Brother," cooed Katherine, "you're so smart! That's why I had to tell you everything. I feel soooo much better now. I couldn't stand to think of having to be a slave to those lesbo bitches for the rest of the year. But I still have this paint all over my butt. Can you help me get it off?"
"How am I supposed to do that? I hadn't really thought about that."
Katherine was suddenly feeling randy again, now that she had potential solutions to her most major concerns. She flashed her butt at him and said, "Does it come off by licking?"
In actual fact, because Alan used a very hard-to-remove latex-based paint, he did have to help in removing the paint. It wasn't easy.
They both got in the bathtub in the bathroom next to Katherine's room. She went in totally naked, while Alan wore his swimsuit. He was much more concerned than her about taking the teasing and touching too far, especially because of his mother's new mood. He was aware that their mother could get nosy and figure out that the two of them were in the bathroom together. But at least the door had an interior lock, which they used.
Katherine lay across his lap. They were as quiet as could be, so their mother wouldn't hear. Katherine was frustrated because she wanted to say things like, "Your cock would feel so much nicer than that brush sliding on my ass," but Alan wouldn't let her whisper, much less moan.
Alan used a rough, Brillo-pad-like brush to scrape her butt repeatedly. Then he used the remote shower nozzle, which was on a hose, to wash away the loose paint. Then they repeated the process over and over. Eventually he got her butt cleared of every last speck of paint, but it took over twenty minutes.
Then she turned over, and he shifted positions and did the same to the front. It finally came down to just her pussy that needed cleaning. She got on all fours so he could get to her pussy and ass from behind.
They couldn't talk, but Katherine could see how he was reacting by the giant lump in his swimsuit.
Her pussy area was the hardest to get clean, because of her pubic hair and pussy lips. Luckily, her labia became fully engorged whenever he brought his hands near them, so that helped expose all the areas which needed to be cleaned.
He tried to gently rub this sensitive area, but even so, the rough brush hurt her a lot.
However, whatever pain she felt was outweighed by intense pleasure. Her clit was fully erect. Alan couldn't resist nudging it each time he passed the brush back and forth. That delighted him, which he concealed from her.
Soon her body was rocked with a series of powerful but extremely quiet orgasms. She leaked profusely as he cleaned her pussy for another fifteen minutes. Finally, it was done.
Once again, he methodically washed off the remaining flecks of paint using the remote shower nozzle. This time, however, he set the nozzle on its most focused setting, using the jet of powerful water as another way to pleasure her.
But when everything was cleaned at last, Katherine didn't move from her position. She simply and silently reached out and grabbed a bar of soap, and then handed it to Alan.
He used the nozzle to make her completely wet from head to toe, then doused himself before turning off the water. Starting at her feet, he worked the bar of soap up her legs, creating a thick lather everywhere his hands went. He lathered her crotch particularly thoroughly before moving higher.
Katherine grabbed his hands and tried to keep them on her pussy as long as she could. Now that he was using his hands and not the brush, she was delighted to find him experimenting with her clit as he rubbed and stretched it. She silently but demonstratively said the word "Yes" over and over, making sure that he understood that he was doing very well.
She tried to guide his fingers into her gash, but he seemed unwilling. So after he'd made her cum several more times before finally moving on to other parts of her body, she took the plunge and began fingering herself.
However, he was willing to plunge a finger into her tight little anus, and soon he was sawing away in that puckered hole while she worked on her pussy. The cleaning was obviously over, and they were both getting carried away with sexual desire.
While Alan had reservations about touching his sister's pussy, he didn't have any problem about touching the rest of her. He continually moved his hands to explore every inch of her that he could.
He thought, I can't believe what's happening! I'm totally, like, nailing her asshole with my finger! And that's not all, not by a long shot. She's letting me run my hands over her ass like I own it!
If this were Mom or Aunt Suzy, I'd be all over it like white on rice. But this is my sister, my younger sister. I should be protecting her from this kind of thing instead of doing it to her! Besides, it's incest!
However, his hands didn't seem to be affected by any of his thoughts. He continued to hold an 'angel versus devil' dialogue in his mind. So what if it's incest? That's true with Mom too, and that hasn't slowed me down with her. Why should it be different with Sis?
I don't know, it just is! Sis is a perfect ten, don't get me wrong. She's one of the sexiest girls in school! But Mom, she breaks the scale. If I were to resist her, that would make me officially gay. And with her so innocent and prudish and all, it's like I'm absolved because no straight guy could possibly resist! Whereas with Sis, she's also my very best friend. What if this screws up our friendship somehow?
But Mom's like my best friend too! We're all so close in so many ways. Why can't we get even MORE close and intimate, like we're doing right now? What's the harm? Besides, she wants it! Listen to her horny moaning!
Oh God! I'm so sorry, Sis! You're just as irresistible as Mom is! Or Aunt Suzy! I give up!
He suddenly lurched forward, so his hands could grasp her boobs. By doing that, his thinly clad boner pressed hard against her ass crack.
Katherine loved that, but she felt it was criminal that his dick was still trapped. She turned around to face him, reached out, and freed his straining hard-on from his swimsuit. She whispered, "You've been so nice, but I should be helping you instead."
By this time, he'd been expecting this, at least mentally, but he was still surprised when it actually happened. Holy shit! Sis is holding my dick! I think she's gonna jack me off! Dang! I don't believe my eyes. And it feels soooo goooood!
Once her hands were on his erection, they didn't let go. Sure enough, she began to stroke him.
She was just as excited about this as he was, if not more so. It was a close call as to whose heart was beating faster and harder. But their feelings were a bit different: they were both extremely aroused and excited, but he was worried and freaking out while she felt a profound sense of relief.
She thought, YES! Home run! Grand slam! Touchdown! Any stupid sports metaphor just doesn't cut it, because this is IT! I've been soooo worried! First, I never thought this could happen, and lately I've been worried that it might but I could blow it, but now it's happening! I actually have my fingers wrapped around Brother's big cock, and I'm totally stroking him! YES! I wish Amy could see this; she'd be way psyched for me!
Ohmigod! It's so hot and hard and long and thick and fleshy and perfect! And Alan! It's all Alan! My brother! The whole room is spinning and I'm gonna pass out, because this is too exciting! We're gonna be lovers! Forever! I'm gonna have his babies!
Those thoughts were so exciting to her that she very nearly did pass out on the spot. She had to close her eyes and force herself to calm down a bit.
At the same time, Alan was busy lathering her tits with soapy suds and generally exploring them. This made her feel so good that it was a great struggle for her to calm her ragged breathing even a bit. She almost had to ask him to stop for a while.
Katherine had been so thrilled by the mere fact that she was stroking her brother's erection that she hadn't really put any thought into how she was stroking it. In recent years, she'd learned from reading erotic stories (usually with brother-sister incest themes) and talking to other girls about sex. As a result, she actually wasn't too bad at stroking it.
So, once she came off the erotic high of her initial euphoria, she tried to put into practice some of the things she'd read about, and thus make her brother feel that much better. One thing she knew was that his most sensitive and arousable area by far was the frenulum, the bundle of nerves just below the underside of his cockhead. In recent days, everyone had called that the "sweet spot," because stimulation of it felt so good.
Katherine stopped making long stroking motions along the full length of his long shaft, and instead concentrated on rubbing her fingers right over his frenulum.
The effect was immediate. Alan felt such a great surge of pleasure that his eyes bulged and he let out a loud, strangled cry.
Luckily, Katherine was mindful about Susan hearing and thus catching them, and she managed to put her hand over his mouth after only a second or two of unrestrained howling.
Seeing that that technique was too effective for their circumstances, she let her fingers wander all over his cockhead instead. That was also very sensitive territory, but a notch or two below direct stimulation of his frenulum.
Their mood changed. Alan had been about to erupt, but Katherine leaned into him and cuddled against his chest, creating more of an intimate and mellow mood. She slowed the pace of her stroking and fondling, and Alan responded by slowing the wandering of his hands over her body, and especially her lovely boobs.
Katherine liked this new mood as much as the previous one, and perhaps more so. It also put her head right next to his ear, allowing her to whisper sweet nothings while she continued to jack him off. "Hey, Bro. How's it going?" She giggled, a bit nervously.
"Um, good." After a long pause, he added, "Your, um... your hand..."
"I know!" She giggled some more, and less nervously this time. "I'm jacking you off. I'm stroking your cock. I'm giving you a handjob! I'm pulling your pud. I'm-"
"Okay, okay," he cut in. "I get the picture! Don't make me feel any worse!"
"Worse? Does it feel bad? I thought I was making you feel good?"
He winced. "You are, but that's the problem! I feel like I'm in Heaven!"
She started licking his ear, but quickly licked her way over to his neck and the side of his face. As she alternated between licks and kisses, she cooed, "So what's the problem? Don't you like it when your cute little sister strokes and fondles your great, big, scary cock? And you must like my tits, seeing as how you can't get your hands off 'em."
He looked down at his hands and felt a wave of guilt. At first he pulled them away, but they came right back mere seconds later. Aw, who am I kidding? Whatever moral reservations I have are getting trampled. It's like tanks versus chariots. I'm neck deep in sexy fun with Mom and Aunt Suzy, and it's gonna happen with Sis too. I know it, she knows it, everyone knows it, so what's the point of feeling skittish about it? It's the natural thing, the next step in our love and our lives. I have to just go with the flow and accept it and even revel in it, instead of fighting it!
He suddenly turned his head. Using a hand to hold her chin, he guided his lips to hers. As soon as their lips locked, they kissed in a way that they'd never kissed anyone else before.
In truth, his reluctance had to do less with worries about incest and more with fear of the unknown. He especially feared that adding a sexual dimension could somehow ruin their close friendship. Plus, he'd already been extremely stressed out about what was happening with his mother and Suzanne, and he felt that he couldn't handle another stressful situation. But kissing her just felt so good and so right that all of his worries seemed to melt away.
Katherine had already felt exhilarated just from knowing that she'd managed to get this far without him getting upset or pushing her away. So to have him initiate an ultra passionate kiss was like a gift from the gods to her. She was so delighted that she felt like she was flying.
Oh, Brother! You love me! You really do! Love me some more! Kiss me forever!
It occurred to him as he kissed her that not only was this his first kiss with his sister, but this was his first mouth-to-mouth kiss, period. It also occurred to him that this was beyond the boundaries which had been drawn by his mother. Even Suzanne had held back in doing so, which puzzled him.
At first, they were both content just to focus on the kissing, as if that were their entire world. But as the minutes passed, they remembered all the other tempting body parts. Katherine in fact had never let go of Alan's erection, and had never even stopped stroking it, but she hadn't been thinking about that at all. But she made his eyes open wide with surprise and a spike of arousal when she resumed jacking it off with a purpose.
Similarly, since Alan was such a tit man, he usually had at least one hand fondling her tits while their necking continued for many long minutes, but he hadn't been thinking about that consciously at all. His other hand had generally alternated between exploring her ass and pussy, and sometimes helping knead her tits, or just running up and down her back, but that also was all on pure instinct. It was only after she resumed her handjob in earnest that he started paying more attention to what he was doing with his own hands to the rest of her body.
She thought, I've never felt this hot before! And my nipples have never been this hard and erect before. Never! I've never felt my heartbeat pounding in my ears like this before either! And I've got his great big cock in my hand, and it's hard because he loves me and wants me! Maybe he even wants to fuck me! It just doesn't get any better than this! I hope I don't have a heart attack from all the excitement.
Eventually he wanted to go further, so he started kissing her jaw line and neck. As he did that, he muttered, "It's no use. There's a part of me that says this is wrong and I should resist, but I can't! You're too beautiful and sexy and tempting. I love you too much! And dammit, this just feels too good!"
She corrected him, "No, it feels too GREAT! Beyond great! Brother, this was meant to be, and you know it! Don't fight it! My hands were meant to stroke your cock. This is who I am: I'm your slut, your sister-slut!"
He was going to protest that, as he didn't want her to use the word 'slut,' much less 'sister-slut,' but she immediately followed her comment with another passionate lip-lock, and they were off to the races again.
She thought as they made out, This! This! THIS is what I want! I want to hold this moment forever! I don't care if it's wrong, or even if he objects; I want to be his sister-slut! Hell, I AM his sister-slut! He's the one I love, the man I would marry if only I could! I don't mind so much that I have to share him with Mom and Aunt Suzy, and maybe even Aims eventually, so long as we can do this every night!
She was so turned on by thoughts of having sex with him every night in the future - for years to come - that she started stroking his cock frantically.
But what she didn't know was that, by this point, Alan's dick had been ready to erupt for so long that even a little more stimulation would push him over the edge. Given her sudden surge of lust, he stood no chance - he began cumming almost immediately. Since they were still pressed tightly together, he shot his seed all over her tummy, up to the undersides of her boobs. His cock pulsed and throbbed as shot after shot of hot semen splattered against her skin.
She was a little freaked out about his cum splattering all over her, but she loved the fact that she was the cause. She continued to stroke his hard rod to coax out the final spurts. After squeezing out every last drop, she rubbed his hot seed into her skin using the remaining cool soapy suds, though most of those were already gone since the two of them had been fondling each other for so long.
Alan finally stepped out of the shower, totally spent.
She silently mouthed the words, "Thank you, Brother," and stood up. She used the shower to get herself wet all over again, in order to wash off all the cum. Then she lathered herself with soap once more, not because she really needed to, but because she knew it would make an extremely arousing sight for her watching brother.
Sure enough, Alan couldn't miss that, even though he was flaccid and still reeling from his orgasm. He stayed for a few more minutes and slowly dried himself with a big towel as he watched his sister sit back down and rinse off her sexy body with a sponge.
He thought, God, she's too young, but I'm so ready to fuck her. She may not have an inhumanly large rack like Aunt Suzy and Mom, but she still would be as good a fuck as anyone in school, I'm sure. And being with her would probably be just as much fun as with the other two, but in a different way. I'll bet she's got a much tighter cunt, for one thing, and I hear that's something really worth fucking. Most importantly though, she's my sister and I love her. That alone would make the fucking really emotionally intense!
Shit! I'm not a bad guy, but how could anyone in my position turn down such beautiful women? If Mother Teresa or the Dalai Lama were here right now, they'd be sticking something into her cunt, I swear. I shouldn't feel bad. There's just no way anyone could resist a display like this!
In the shower, his sister spent much more time with her hands roaming over her pussy and breasts than she did rinsing off the soap.
He was amazed that her pussy could take so much rough stimulation in such a short time and still apparently want more.
As if reading his thoughts, she turned towards him and winked invitingly. Between what had happened at school with Kim and the fulfillment of her long-time fantasies with her brother, she felt sexually insatiable.
He left before another round of fun could begin. They'd already spent an outrageous amount of time in the bathroom. With Susan home and in the kitchen, it was a near miracle that their time together hadn't already led to trouble.
The day's events with Katherine had erased Alan's earlier depression over what had happened with his mother. Although he was no longer getting help from his mother, or openly from Suzanne, he'd found in his sister someone else to occupy his thoughts and keep him horny while his father was at home. He looked forward with great anticipation to additional sexual hijinks next week at school, since he now knew that he would secretly be painting both Katherine and Kim for five days in a row.
An hour after their time together in the tub, Katherine came up to Alan in his room, and said, "I really want to thank you for all you did to help me today, Bro. I really mean it. Even though I got into a lot of trouble, it would have been ten times worse without you. I don't want to just tease you either; I'm sorry if I went too far. You know what Mom says about boundaries. What if I treat you to a movie tonight, as a small way of saying thanks and to beg forgiveness for being so over the top?"
"That sounds nice, Sis, but I already have plans with Christine tonight. How about tomorrow night? I imagine we'll be having dinner with Mom and Ron, and then after that I'm sure we could get away for a late movie." (Because his father was seldom present and didn't interact with him like a dad, Alan made it a point to just refer to him as "Father" rather than "Dad." But now that he was competing with Ron for Susan's sexual favors, he preferred not to acknowledge that relationship, so instead had started to call him "Ron" as if he were just a competing boyfriend.)
"Tomorrow sounds great!" said Katherine enthusiastically. But, in a much more subdued and concerned tone, she added, "But what's this about you and Christine? I thought that went down in flames."
"It did. But we went from the game to get some ice cream together and things were okay. It was very awkward the first time that we talked at school after it happened, but we overcame that once we started talking about homework and school stuff."
"I see." Her face was lined with worry, but he was oblivious to it. "So does that mean you might get together with her in a more serious way?"
"Nah. Are you kidding? Asking her out was a complete nightmare; I think I'd rather have root canal surgery than try that again. I think she knows that I'm not thinking of her in, you know, that way, anymore."
"At least you're trying not to think like that."
"True. I'm trying. I must admit it's a lot easier to get her off my mind with everything else that's been going on around here! Anyways, she's just trying to show that she has no hard feelings and that she still wants to be friends. Maybe that'll allow us to become even closer friends than we were before."
"Cool. That's great," said Katherine. She was very relieved to hear that. However, she was still very jealous that Alan was seeing Christine, no matter what the reason.
Katherine knew that she wanted to go all the way with her brother. For her, helping him with his "problem" would just be a step on the road leading to sex with him. She wasn't sure exactly when she had crossed over from unlikely fantasy to what had become an urgent need, but certainly by the time he drove her insensate with desire with the Brillo-like brush, she knew absolutely that she wanted him to fuck her, and soon.
So she went back to her room and wrote in her diary.
Today was so GREAT! Sure, what happened with Kim and Heather wasn't good, but I'm not THAT worried about it. True, Kim acted pretty weird, but I think she's basically a nice person and just got carried away by all her sudden power. I bet she'll go back to normal before long. At least, I hope so! Heather is a much tougher problem - she's SUCH a BITCH! But Brother says he's gonna help. He can be my knight in shining armor, saving me from the evil queen! Hee-hee!
All things considered, I'd have to say I'd totally make all those mistakes again, 'cos it totally brought Brother and me way closer! He got soooo intimate with my pussy today that I can't even believe it! He spent, like, HOURS painting my pussy and even playing with it! Diary, I know you can't see it, but I'm getting REALLY horny right now! There's a lot of one-handed writing going on, if you know what I mean!
I know I'm a freak, because I'm head over heels in love with my own brother and I want him to fuck me, but I don't care! He's the nicest, best-est guy I've ever met, and I can't help that we're related!
Diary, you know how long I've dreamed and fantasized, but today it's all really coming true! I don't know if he's in love with me more than the really close sibling love we already have, but he obviously lusts for me, and that's a way good start! Hee! This whole painting thing can be my foot in the door to even more sexy fun with him!
Nothing can stop us now. Well, except maybe for Christine. The fact that he would go on a date of sorts with her makes me REALLY worried! She's beautiful and intelligent and she's got those damn boy magnets - her gigantic boobs! Perhaps she doesn't like how Bro's not acting like a pathetic puppy dog around her, now that she's turned him down? Maybe she's changed her mind? If so, I'd better act fast before she makes a move. I don't need any more tough competition! I'll have to come up with some sort of plan to speed up Bro's seduction!
Once he starts fucking me, he'll still be getting handjobs and blowjobs from Mom and Aunt Suzy, and between the three of us we can keep him totally sexually satiated, if not completely exhausted! One guy with three sexy, busty women, living in the same house? He'll be too tired to even THINK about Christine! I just need to milk this whole painting situation, and milk him too! I'd better use every opportunity this next week to wear down his resistance and get very close and personal with his cock! If all goes well, I'll wear him down and overcome his resistance completely in the next few days, and then we'll be fucking!
Aunt Suzy and Mom have both been giving him blowjobs, but nothing more. And now Mom at least seems to have even stopped that for the time being, so he must be frustrated and desperate to go all the way. This is my window, my chance to get an edge on those two. Anyway, if I don't go all the way, I can't compete with their extreme beauty, and then he's gonna forget all about me.
It's going all the way or bust!
— — —
Katherine didn't waste any time. She put her diary away, put on some conservative clothes so she wouldn't scare him off, and went across the hall to his bedroom. She came in just after Alan got up from his bed and went to his computer to do some homework. She said, "Hey, Bro. By the way, you know about teasing and boundaries. I realize we need to take it a bit easy. But don't you think what we did in the bathroom earlier was okay? Can't we do that again without Mom knowing?"
He swirled around in his desk chair to face her. "What, you mean when you...? With your hands...?" He was too embarrassed to talk about getting a handjob in front of his sister.
"Cat got your tongue?" Katherine asked, delighted by his bashfulness. "Or has Kat got something else of yours? I'm talking about this here - this thing in your shorts." She put her hands on his hard-on through his shorts.
His only reaction was to get red in the face.
Emboldened, she knelt in front of him and undid his zipper.
His penis was already extremely stiff. All he could do was moan "This is wrong!" as she took his shaft in her hands. But he was unable to offer any more resistance than some worried whimpering.
She ignored his hesitancy, flashing a big smile at the long dick that sprang out of his shorts. She thought, I'm going to get to know this thing very, very well. Yes indeed! I can almost imagine what it would feel like to have it pushing in and out of me. What a dream come true! Even now, if he imagined how many times I fantasized about walking down the aisle of a church holding his hand, he'd freak.
But to Alan, she merely asked, "If I give your cock some relief from time to time, isn't that just what the doctor ordered? Mom doesn't need to know."
"I don't like going behind Mom's back; I don't think we should do that," he said weakly, seeming to forget about everything else he'd secretly done with Katherine earlier in the day, including the fact that she'd just jacked him off a little while ago.
"Well, think about it. In the meantime, let me thank you for your help in another way. It's not like I haven't done this to you already, same as Mom and Aunt Suzy. Or have you forgotten what happened in the bathroom? We can just draw the line here..."
She opened his knees wider and squeezed in closer so his cockhead practically bumped against her nose.
He held his breath because he was so mesmerized by the sight of his erection framed by his sister's beautiful face.
Then she began stroking. She held it so close to her mouth that she deliberately teased it with every breath she took.
Despite all her assertiveness and bravado, she was still incredibly nervous in a new situation like this. She was excited but scared, like parachuting out of an airplane for the first time. And she was worried that she wouldn't please Alan as much as a more experienced woman like Suzanne could. But she did her best, and slowly relaxed as she received Alan's silent encouragement and acceptance.
He was extremely nervous too. He was torn between lust and a lingering sense that their incestuous contact was wrong. He bargained with himself that a handjob was okay due to his medical problem, but a blowjob from his own sister was going too far. Since Katherine kept the tip of his erection so close to her mouth that she could have stuck her tongue out to lick it at any time, he focused his worries on that.
She was still fully dressed, but she didn't stay that way for long. Once she was confident that she had him in the palm of her hand (in more ways than one!), she took some time out to take her top and bra off.
He was going to protest, until she brought his hands to her breasts and let him fondle them.
As she resumed jacking him off just inches from her face, he complained, "I'm so weak!"
She replied, "No you're not! In fact, you're so strong and persuasive that you've got Mom, Aunt Suzy, Amy, and me all hot for your cock!"
He complained, "I've hardly done anything. They just come after me. It's this weird six-times-a-day treatment."
Katherine wasn't sure what was happening between Alan and Amy, so she had added her name as a kind of fishing expedition. The fact that he didn't question it gave her a clue that something really was happening there.
She joked, "I call Dr. Fredrickson's treatment program for you the best medical diagnosis in history!"
He smiled, but said, "Shhhh! Keep it down, please. You don't want Mom to hear us!"
Katherine kept blowing on his cockhead as well as stroking it. "Yeah. If she came in, then I'd have to share, and I want this big fat cock all to myself! I can totally picture it now: she'd come in and look all alarmed at first. She'd raise her hands over her titanic tits, and mutter something like, 'Oh my goodness! This is so improper!' But her giant boobs would start heaving anyway, and her face would get all flushed and red with arousal."
"Sis, please! Stop!"
But she ignored his plea. She knew on a rational level that she was one of the most beautiful girls in school, but she nonetheless lacked self-confidence about her own appearance. At the same time, there was no way to deny their mother's extraordinary, voluptuous beauty and her brother's lust for her, so Katherine used that to advantage. "You know how she is. She'll keep complaining about sin and all that crap, but she's drawn to your cock like a moth to a flame. Within minutes, she'll take her blouse and bra off, letting her huge hooters bounce free!"
He was getting sweaty and was panting hard already. But still, he asked, "And why on Earth would she do that?!"
"Because she's hot for your cock! I saw the way she stared at your erection the other morning. I don't know what excuse she'd use. Maybe she'd suggest you need some quote, visual stimulation, unquote. But mark my words, she'd be topless, if not completely nude, before long! Then I'd have to scoot over a little bit so she could help stroke your cock!"
"NO!" he cried out. It wasn't that he objected; it was that her words were so arousing to him that he wanted to deny them in a futile, feeble attempt to stop himself from getting too overheated with lusty need.
Seeing that she was on the right track, she continued her fantasy with growing excitement, while she kept on stroking and breathing on his cock. "It's true! But luckily, your cock is so long and thick that there would be plenty of room for her hand AND my hand. In fact, I'd probably lick it a little bit, like this."
She paused in her story, and tentatively licked the very tip of his cockhead a bit. She found the taste of his pre-cum not at all unpleasant; it was actually surprisingly nice.
But he cried out "NOOOO!" even louder. He didn't want the joy to end, but he knew it would if she kept on doing that.
She was forced to stop after just a few licks. For one thing, he was protesting far too loudly, and she didn't want Susan to come in for real. But also, it was clear that he was increasingly close to a great climax, and, just like him, she didn't want to overstimulate him and have the fun end too soon.
So, since she was taking a time out anyway, she took off her skirt and panties. She knew she had him in the palm of her hand now, so her confidence was growing. She preened and posed a little bit as she finished undressing. "Are you ready to cum yet? I'm thinking I'd better take everything off, just in case you cum on me."
He groaned helplessly. He muttered, "Too hot!" He was almost afraid to look at her, because she was that gorgeous and he was that close to cumming.
She got on all fours this time as she moved back to his crotch. She took his boner in her hand and asked, "What's that? Did you say something's too hot? Hmmm... What could be too hot? Oh, I know! It must be your cock. Here, I'll help cool it down some." She resumed blowing on it. With her mouth only an inch or two away from his sensitive cockhead, her powerful breath drove him absolutely wild.
He didn't want her to blow that much, because it was more than he could handle. So he confessed, "No! Not that. You! You're too hot! Damn, you're beautiful!"
She beamed. "Awww! You're so sweet, Bro. Aunt Suzy's right. You're a real sweetie. Just for that, I'm gonna blow even more, AND pump on your shaft like there's no tomorrow!" She started making good on that promise.
She giggled as she stroked. "Did you just say 'gaaack?' What does that mean?"
He desperately panted, "Too... Too much!" He'd been keeping his eyes closed because of overstimulation, but he briefly took a peek at her. He saw her big boobs dangling down and swaying in time to her stroking, and it was too much to bear. He squeezed his PC muscle frantically and closed his eyes again.
She giggled some more, but she stopped her story for a while and let up on her stroking, for fear that he was too close to cumming.
But when his breathing returned more or less to normal, she resumed, noting, "You know, this is pretty easy! I think I'm getting the hang of this cock-stroking stuff. I mean, it's not rocket science. I just stroke my fingers up and down through all this squishy pre-cum, and sometimes in a corkscrew motion, and you pretty much have a heart attack. What do you think?"
He gasped out, "The sweet spot!"
She grinned wickedly. "Oh yeah! This spot here, right?" She licked up and down over his frenulum, but only once, because she knew he was extremely close to cumming and she was pushing her luck. "Is that what you mean?"
He nodded, but then said, "Yeah, but you're stimulating it too much! Too ... arousing!"
She giggled. "Oops! Then you probably don't want me to breathe all heavily on it, like this." She managed to blow continuously on his sweet spot from only an inch away, as if he'd been burned there and she was trying to cool it off with a steady flow of air.
He whimpered helplessly. He was sweating bullets, even though he was just sitting there, perhaps because he was flexing his PC muscle for all he was worth.
Seeing the desperate state that he was in, she backed off again. She thought, This is soooo much fun! Forget about how good it feels to hold his big cock and slide all over it with my wet fingers - I love how I'm kind of controlling him! I mean, I just need to do something extra arousing and I'm instantly rewarded with an extra sexy moan from him! Like this... She blew again on his sweet spot, while rubbing two fingers over it at the same time.
Sure enough, he responded with a moan that was so desperate and lusty that she was nearly certain he would cum on the spot.
Somehow, he held on, but only just. The PC muscle technique really did work wonders for his stamina.
See? That is soooo cool! She still didn't want the fun to end, so she all but stopped her stroking and blowing, and just held his boner in her warm hands, giving him a chance to calm down again.
But it wasn't much of a break for him, because she resumed her narrative about their mother joining in. "Wow, I love the way your cock feels so hot, and trembles in my hand. Does Mom love that too? I'll bet she does. What kind of stuff does she say to you when SHE has your big cock in her hands?"
He was too far gone to realize how much she was deliberately trying to drive him wild with her talking, so he answered honestly, "Uh, she doesn't talk that much."
Katherine eagerly replied, "I'll bet that's 'cos she's too busy sucking your cock!"
"Shhhh!" he moaned. "Not so loud!"
She continued at a lower volume, "Imagine that she's kneeling next to me, like I was saying before. She's ready to take her cocksucking turn! Picture four big tits all lined up in a row for your pleasure."
He groaned helplessly, especially because he was picturing just that. He felt that he was going to cum any second, despite his frantic efforts to hold back. It didn't help that his sister had resumed fondling his shaft.
She spoke enthusiastically. "You know it's gonna happen for real, and soon! So, Bro, my question is, when Mom and I are sharing your cock, probably every morning, afternoon, and night, do you think she'll talk then, or will she still be too busy running her tongue all over your fat boner? Will I be forced to suck and lick it too, just to keep up with her? And what about Aunt Suzy? Do you think there's room between your knees for all three of us to stroke it and suck it at the same time?"
As she spoke, she felt his balls pulling up, and realized that he was going to cum in a matter of seconds. Since he was past the point of no return, she jacked him off with greater speed.
By the time she mentioned "Aunt Suzy," he indeed was past the point of being able to hold back, but adding her to the fantasy was like lighting a rocket booster on an already speeding race car: the cum suddenly blasted out of his dick like it was attempting to launch into orbit.
Katherine had been so focused on teasing and stimulating him that she hadn't given any thought to what she should do when he actually started to cum. She briefly considered letting him cum on her face or breasts, but that seemed kind of gross to her, so she frantically looked around for alternatives.
Unfortunately for her, there was no time for alternatives. His hard-on was mere inches away from her face, so he started shooting at that. Once the cum hit her face, she figured she really had no choice but to take it, so she shut her eyes tightly. She'd heard (correctly) that cum in the eyes could really sting.
Then it dawned on her that he could cum on her breasts instead, so she aimed his dick lower. Once she did that, she dared to open her eyes and look around.
She was captivated by the sight of his erection twitching and firing like an out-of-control fire hose. Knowing that she had stiff competition from their mother and Suzanne, and maybe eventually even Amy, she made sure to keep stroking him until his climax was all over.
Only when he was done did she notice a towel within reach. She was chagrined, because by that time it was too late for the towel to be of much help.
After he'd finished cumming, she still didn't want to let go. She continued to slide her hand up and down his now slimy, cum-coated shaft as it slowly lost its turgid state.
She also ran a finger through a long strand of cum streaking across her left cheek. "Wow, Brother! Impressive! Look at what you did to me: you've got my hands practically drowning in all your sticky goo, 'cos I can't seem to stop stroking your great cock! And you've got even MORE of your pearly baby batter on my face. And then look at my boobs!"
She sat up on her heels, giving him a better view of the cum on her face and chest. "Check this out!" She ran a finger across the upper slopes of her bare tits, leaving a streaky trail through the pearly mess. "Look at ALL this cum! It's so much! Do you always cum this much into Mom's mouth? Or Aunt Suzy's?"
He admitted between exhausted pants, "No, Sis, not usually. You inspire me. Jesus! It's like you're trying to kill me with too much arousal! Have mercy! Please!"
Fascinated, she kept on running her fingers through his cum streaks.
He had to close his eyes tightly, because the sight of his cum on her fingers, chest, and face actually made his head spin.
She loved that she'd made him cry mercy. This is just about the most fun I've ever had in my life! Seriously! I can't wait to tell my diary all about it.
She couldn't remember ever enjoying something else as much as making him cum. She wanted to do it again. Even though his dick had gone flaccid, she took it back in her hands. "Soooo, Bro... Tell me... Do you like cumming on my face?"
He was still needy for air, but he managed to gasp out a reply. "Damn! I love it!"
"What about on my boobs?"
"Love it too!"
She wasn't sure what she thought about all of this cum on her skin. If he loved it so much, she figured she could at least pretend to enjoy it. The main thing was that she wanted more cum from him; where it ended up was just a side issue. She cooed, "Well, then you'll just have to paint me with another load or two."
He panted, "Can't! ... Dick hurts. ... Need ... to rest."
She took mercy on him and let go of his penis. She realized that men did have their limits.
Even though Katherine had experienced a little taste of his cum earlier, she was still hesitant to actually lick any of it, so she used the towel to wipe off most of it before heading to the bathroom to wash off the rest.
It turned out that Alan didn't have much time to recover, because he had to get ready for his "non-romantic" date with Christine. They already had plans to have dinner and see a movie.
As he left to pick up Christine, he thought about her. You know, it's ironic. Before she shot me down, we were friends, but just school friends. We never did anything outside of school together, like, at all. And now that she's rejected me, we're basically going on a date to patch up our friendship, the very kind of date she shot me down over! But the key difference, sadly, is that it's understood that this is a completely platonic date.
Alan picked up Christine at her house, and was surprised to see that she was dressed as if she were going on a real date. He had dressed somewhat nicely, wearing a collared shirt and slacks for a rare change from his usual T-shirt and shorts, but she had really outdone herself. He'd dreamt about seeing her cleavage countless times, but he never had, not even when she was wearing various sports clothing. She was very scrupulous about wearing high necklines, which only added to her mystique with the boys. But now he could see her tantalizingly deep valley in nearly all its glory.
His dick immediately got hard, extremely hard. Although he was resigned not to pursue her romantically, he still got intensely aroused almost every time he saw her.
As he came up to her, he said, "My gosh, Christine, you look absolutely fantastic!"
But then realizing this wasn't supposed to be a "real" date, he joked, "In a completely platonic sort of way, of course."
She laughed at that. "Thanks. Do you really think so?"
He joked, "I try to, but you make it hard whenever I'm around you."
He belatedly realized the double meaning in his words and thought to himself, And I definitely do mean that in more ways than one!
She laughed again, but a little nervously this time, because she caught both meanings. Still, she was insecure about her looks, remarkably enough, so she eagerly ate up his compliments.
He piled it on. "I'm serious. You look so ... womanly. So mature. I've never seen you in a skirt - it turns out you have legs! I was pretty certain you had feet, but beyond that I wasn't so sure."
She laughed some more. "Do I dress that badly? Maybe I need to wear shorts and skirts a little more often."
"Please do. Don't hide your legs because... What legs they are! And you've got a purse, like a lovely lady. Lipstick, even! And is that rouge on your cheeks? Wow! I'm honored to be with such an enchanting creature. But with you no makeup is necessary because it's impossible to improve on perfection." He wanted to compliment her cleavage as well, but he didn't know how to do that without sounding like a letch.
She was smiling broadly now. "Stop that ... eventually! I'll give you two hours to stop the flattery. Seriously, you know I really meant it the other day when I said I'm not ready to go out with anybody. Right now I can't let anything distract me from getting into the college of my choice."
"You know you're already a shoo-in anywhere in the country." He was certain about that.
"Don't be so sure. This semester will be the most crucial. I figure this is probably going to be the closest thing to a real date for me in a long time, so I wanted to go all out. I hope you're not weirded out or getting the wrong idea or anything?"
"Absolutely not. I'm just platonically delighted to be spending a lovely evening with a very lovely lady. Emphasis on platonic." He looked jovial and gave her a friendly wink.
With over-the-top theatricality, he made a sweeping bow and then held out his hand. "Come, my lady. A big fat evening of fun awaits." He was making a joking reference to the fact that they had plans to see the movie "My Big Fat Greek Wedding," and then have a late dinner afterwards.
He thought, Man, I just hope she doesn't notice "My Big Fat American Penis!" These slacks aren't good for hiding my raging boner, and she'd probably get offended. But what does she expect, when she looks that great?!
She took his hand and stepped towards his car.
But to her surprise, he kissed her hand before walking her to his car, arm in arm.
Although his gesture was unexpected, she wasn't concerned. It was obviously just a fun kiss, not an "I'm trying to get in your pants" kind of kiss.
He said, "To be honest, I haven't exactly been on a lot of dates myself, and my prospects don't look so hot. So I figure this can be a kind of fun practice date for each of us. Don't mind me if I ham it up."
"Mind? I think it's great. And I love the 'practice date' idea. That's a good name for it."
Just as he was about to start the car engine, he said matter-of-factly, "By the way, this is a car. More specifically, it's my family's minivan. A car is something that takes us places quickly."
She looked at him like he had two heads. "What the hell are you talking about?!"
"Oh. Well, I figured that since you're blonde, I need to explain the basics. But I'm probably using big words that you don't understand. Let me try again: This. Is. A. Car."
She reached over and hit him on the head, but she was secretly amused. She didn't find his Dumb Blonde jokes sexist, because she knew he wasn't like that, and in fact he only used those jokes on her. It was more of an ironic commentary on the fact that she was, by far, the smartest person he knew.
"Ow! That hurt!" He reacted like she'd seriously punched him, when in fact she'd hit him with the force of a typical slap. This was part of their routine: he'd tell a Dumb Blonde joke, she'd act offended and tap him lightly, and then he'd pretend to be mortally wounded. It was silly and predictable, but they both enjoyed it.
As they talked and joked, Christine thought, What's gotten into Alan? This is great! He's so much more confident than before. Is this the same guy who was slumped down and afraid to look me in the eye when he asked me out last month? I thought things might be weird, especially with the rather bold way I dressed, but he's completely at ease, and that puts me at ease too. Could it be that he's finally over me, and because of that he's not all fumbling and nervous around me anymore? I hope so. I like this new Alan a lot more than the old one.
Little did Christine know, but there was a different reason for his greater confidence and more overt masculinity: all the fantastic sexual encounters he was having with the gorgeous women at home had pretty much obliterated his fear of being close to beautiful women.
In fact, as they got into his car he secretly marveled at how he could rub his sister's dripping pussy with a brush one hour, then innocently chat with Christine an hour or two later. It all seemed so surreal, yet wonderful. He thought, To think: not long before this "practice date" started, Sis gave me not one but TWO handjobs! Kat, of all people! If Christine only knew, she'd literally kill me! Yet here I sit, cool as a cucumber. I'm getting really dang good at rolling with the punches, that's for sure.
The "date" went well. Neither of them liked "My Big Fat Greek Wedding" much, finding it too lightweight and plotless. But afterwards at dinner, at a thematically-appropriate local Greek restaurant, they had a lot of fun analyzing it and tearing it apart.
There was no mention, no matter how oblique, of what had happened when Alan had tried to ask Christine out. There were no serious discussions about where they stood with each other. Instead, they just kept it light and had fun.
The only snag Alan had was that his penis stayed erect more often than not. True, the tantalizing glimpse of Christine's cleavage was a big factor, but he figured he would have been aroused no matter what she wore, just because he was with her. When she finally loosened up, which could take a long time, she could be surprisingly charming and witty.
He was so happy being with her that he started to suspect he was still in love with her. He wondered how that was even possible with all the other exciting things happening to him lately, but there was no explaining love. Still, he didn't let himself pursue that line of thinking, since he was trying hard just to have a good, non-romantic friendship.
When Alan dropped Christine off as the evening ended, he again was over the top with his chivalric gallantry. But it served as a good excuse for him to give her a good-night kiss on the cheek at her front door.
As he drove home, he thought, That was a blast! But the whole thing is so ironic. The only reason I could be so witty and charming is because I now know there's no romantic possibility between us. Otherwise, I would have been a nervous wreck. But as a result of my new attitude, we clicked so well that it started to seem like there WAS something romantic between us.
I mean, with that goodnight kiss I got the impression that Christine wouldn't have minded terribly if I'd kissed her some more. She kissed me back, nearly on the mouth, and then almost looked sad when I pulled away. Or was that look just my imagination? I don't know. Probably just wishful thinking on my part. I wish I had more experience with things like this!
In any case, it's a moot point. It's too late for us to be a couple because of all the crazy stuff that's happening to me at home. She'd never allow that to continue if she knew - not that I could ever tell her! - and I love it too much to stop. All of a sudden, I've got more girls than I can handle, which is yet more irony. A few weeks ago, I felt like I'd be celibate and single forever. As much as I loved Christine, I love Sis a lot more. But still, maybe Christine and I can do this kind of thing more often and just have a nice time together, now that the romantic pressure is off.
So, before his memory of Christine faded, he jacked off another two times.
Christine also ruminated after Alan left, What has gotten into him? I could get used to fun evenings like this one. Before, he used to make me nervous with the way he'd be anxious around me and always stare at my body, but tonight he put me at ease and made me feel good about myself. Now, I just know I'm gonna be smiling for hours. I wish I would have known he could be like this before I turned him down.
Did I make a mistake?
NOTE: Thanks to the suggestions and corrections of OmegaZone, Spurtz, EBC, Gnome, IBT, WD40, NightShadow, Sam.I.am, Even, Magoo, NickS, Orestes, Mick, BamaPolyBiGuy1, Jamielynn, greyshadow, Sir J, AmyFanatic46, and AkhtariEl. The longer dumb-blonde joke was courtesy of Jimmy the Saint.
A special thanks goes to YamiBoy for colorizing existing illustrations. MagicMan also assisted in improving the pictures. Special thanks to Magoo and BamaPolyBiGuy1 for remarkably thorough and repeated proofreading. And finally, an extra special thanks to Sam.I.am for coordinating and processing all of the proofreading input.
It is not the author's intention to infringe on anyone's copyright. If an image copyright holder finds an unauthorized image within these illustrations and wishes it removed, we will do so immediately. We will not respond to hearsay or assumptions, only to originators or their authorized agents. Thank you. Spacer X