6 Times a Day

Drunk Dargon Special 🐉 [ 12 / 12 ] 3K words

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Heather gave Alan directions to the theater room, so he went right there on his bicycle and then locked his bike up nearby. Alan had never been in that room before, since it was in a little-used part of the campus and always locked. He had to knock to get in, because now that Heather had access, she was very careful to make sure the door stayed locked.

He was surprised that there was such a big, unused room in their overcrowded school. Apparently it couldn't be used as a classroom because the floor sloped slightly, providing stadium seating (where the back seats are higher than the front seats) before the seats had been removed. An un-level floor was hardly ideal for cheerleading practice, but Heather figured secrecy was more important. Besides, it was flat just in front of the stage and on the wooden stage, so they had plenty of space. It was a very big room indeed.

Practice stopped when Alan entered the room. The mood changed because everyone was curious about what he'd do. He was briefly introduced to the other cheerleaders, but in fact he knew them all by name already except for Janice and Joy. He looked around the room and thought, Dang! I'm sexually involved with ALL the cheerleaders except for Janice and Joy. That's pretty cool!

Heather looked at Alan and smirked. She walked up to him and spoke quietly near his ear, so only he could hear. "How do you like the room? I've got the only key, and official permission to use it. Soundproof walls, perfect privacy. It's the ideal place to give a naughty slut her well-deserved reward, don't you think?"

She stepped back and flashed him an even more knowing and seductive smirk. She loved the blindsided look on his face.

He thought, Dang! How the hell did she find a room like this? So much for my plan to say her private spot isn't private enough. Damn! This changes everything.

He felt aroused by the prospect of fucking her in that room in the near future, but he also worried. He could never permit himself to forget that she was really dangerous to his family, and that he was supposed to be winding down his sexual relationship with her.

Speaking loudly again, she said to him, "See her? That's Joy. She's the one you have to paint." She was surprised at how difficult it was for her to act normally around Alan, but she was good at hiding her emotions. Even so, she found it surprisingly hard to suppress her desire to hug and kiss him.

Alan looked at where Heather pointed and briefly checked out Joy. She was rather short compared to the tall females Alan was used to, but she was not as short as Kim. She looked like the stereotypical brown-eyed, brown-haired, lightly-tanned California cheerleader. Overall she had a nice body, but nothing really stood out. Her boobs were, if anything, average or less than average. But she had very big brown eyes and a really winning smile. She briefly flashed him her smile and acted as if everything was normal, but quickly went back to acting worried and nervous.

Alan decided the best way to handle this extremely odd situation was to be quick and business-like. "This is really awkward for everybody, I'm sure, so let's get this done as fast as possible. I'm going to be strictly professional about this. Joy, please take off your underwear, then turn around and tie this string around your waist to hold up your skirt. We need to keep that completely out of the way."

Joy reluctantly did as she was told, even though she trembled in fear. Her eyes were clenched closed, fiercely tight.

"There's nothing to worry about," Alan said as he tried to calm her while gathering his supplies. "Just imagine you're a marble statue and I'm a painter painting the marble. Like I said, even though I'm a guy, I'm going to be completely professional. I've painted both my sister and Kim in a completely nonsexual way, so I can do that to you too." His words had a definite calming effect. "This is already old hat for me. And you can be sure I won't snitch to anyone about anything."

That last comment seemed to strike a nerve, causing her to sob a bit.

Heather pointed out, "Joy is getting punished because she told someone about what happened to Katherine and Kim. But luckily that person didn't tell anyone else."

"Oh," said Alan as he realized what he'd said to set her off so abruptly. "Sorry. I'm going to start painting your rear end now. Are you okay with that, Joy?"

"I guess so. Please hurry and get it done."

"I'm hurrying. The first thing I'm going to do is draw the outlines with this small brush and then I'll fill in the rest with a bigger one." He began to paint quickly.

The rest of the cheerleaders gathered round and watched with great interest. Only Katherine and Kim had seen any panty painting before, and both of them had been too busy with each other or with Alan to really watch how he did it, so even they were interested.

Alan finished Joy's backside in record time and, after a few minutes for it to dry, had her turn around. She put her hand over her bush and squealed, "Please don't look at that!"

"Sorry, Joy, but I have to," he said reasonably, with a sympathetic look on his face. "How can I paint without looking?" He gently placed his hand on hers and moved it away.

"I'm just so embarrassed!" Her friend Janice took one of her hands and Kim on her other side took the other. Together they gently stroked her hands and comforted her.

Alan put the paint aside momentarily. "Okay, Joy, before I go on, you need to get shaved. I've never shaved, um, one of these before," he lied, in an effort to make her feel more comfortable. He hoped that if someone else could do it she might relax, so he asked, "Does anyone else want to do this part?"

There were no takers. Katherine and Heather, who normally were bold enough to have helped, wanted to see him shave Joy, so he could push things further along with her.

So Alan began to shave Joy's quivering mound. As he did, her aroma began to waft up to his nose, forcing him to fight valiantly with himself to ignore it. "I guess it's not that different from shaving my face. Could someone talk to Joy while I'm doing this, just to distract her a bit and help her relax?"

Kim and Katherine talked to her, telling of their own experiences of being a shaved cheerleader without underwear. But they stressed only the positives and, needless to say, omitted that Alan had shaved either of them (as well as all the sexual antics that had later occurred).

Joy made brief comments and asked a few nervous questions.

It took a while for Alan to shave Joy. He went to great lengths to avoid touching her private parts, but some contact couldn't be helped. He touched her clitoris a couple of times, and had to wipe off the last of the shaving cream from her skin with his hand. But he generally maintained as professional and dispassionate an attitude as anyone could have hoped for in such circumstances. It helped that Joy was too nervous and shy to get even slightly sexually excited, so her pussy wasn't wet and her pussy lips weren't engorged.

"We're all done with the shaving," he eventually announced. "Does anyone have a mirror, or even two?" It was no problem to find a couple of mirrors, since the room was filled with cheerleaders who obsessed over their looks. "Here, see how it looks," Alan said as he handed a mirror to Joy.

She held the small mirror away from herself, nervously positioning it until she got the angle right to see her own bare pussy. "OH ... MY ... GOD! I'm soooo embarrassed!" She closed her eyes again and put her hands over her face, as if that would make the naked privates go away.

Alan then got to work on touching up the paint on her butt, now that the primary painting had dried.

After a few more minutes of cajoling, Joy was convinced to look in the mirror again. This time they also positioned the second mirror behind Joy so she could look at her painted butt. That caused even more squeals of mortification.

The other cheerleaders watched all of this with rapt attention. Already a good fifteen minutes had elapsed.

Alan was finally able to move on to painting her front. He painted it all quickly, including most of her shaved pussy.

But after all this painting of private parts, Alan found his nobility slipping a bit. He decided to push things just a little, both out of selfish desire and because he simply had to in order to get the job done right. So before he was done with her pussy, he said, "Uh-oh, we have a problem."

"What is it?" Heather asked.

"When I painted Katherine and Kim, they were both ... sexually excited at the idea of not wearing underwear in front of a big crowd. That would excite anybody, I thought." It was true that they'd been excited, but much more by the fact that Alan was painting and touching them, but of course Alan didn't mention that part. "But Joy is so frightened, I guess, that she's not excited at all. So her, uh, nether lips aren't aroused. That means I can't paint very much of them. Which means that if the game comes and she gets excited, then a lot of pinkness will be exposed and it could be highly embarrassing."

"Hmmm. I see," Heather said. "Can you do something about that, Joy, and open up your pussy lips? Maybe hold them open?"

"What, right now?!" she asked in total amazement. "No way!"

"Well, do you want him to paint that part, or would you rather be pink for the game?"

"I-I-I-I guess, paint that part. But I just can't do it right now! I'm so embarrassed, I'm ready to die!"

"Okay, okay, relax," said Heather calmly. Turning to Alan, she asked him, "Katherine probably told you this would be a one-day thing, but could you come back tomorrow to touch up that part?"

"No way!" he protested. He was hoping by pressing the pussy lips issue he'd maybe get to see someone stimulate Joy, rather than him being forced to come back. Being with his sister in such a situation was too dangerous; secrets might come out. He said, "I'm pushing my luck doing this kind of thing. Do you realize the risk I'm taking? And for what? Just to be nice and do you all a favor. What if someone came in right now? Don't even make me think about it!"

Heather said assuredly, "No one is going to come in. You know the school is deserted on a holiday like this."

"Hey, anything is possible," he said. "Maybe the very fact that nobody is supposed to be here would cause the janitor to come investigate. I've got my bike parked out front, you know."

She replied, "Why would the janitor or anyone else be working today? You saw that the door is locked. Face it, we have perfect privacy."

She flashed him a knowing, sexual look, as if to say, I want my reward, and I want it now! This is where you're going to be fucking me soon!

Alan was rightfully dubious about her claim to have "perfect privacy." He knew that there were all kinds of practical problems and risks with having sex anywhere on school grounds. It seemed more likely that she was simply trying to put his concerns at rest so they could get down to some sexy fun. He decided not to challenge her on it, since he figured he had little to no chance of getting the truth out of her easily.

She asked, "Anyway, what about lunch time tomorrow?"

"Well... I guess. I'm busy at the start of lunch tomorrow, though." He tried to figure, How can I possibly juggle this with my sexual session with Glory tomorrow? Ah well, I'll cross that bridge when I come to it.

He concluded, "Maybe ten or fifteen minutes into lunch I can come by for a few minutes, I guess. But, please, let's not make a habit of this!"

Heather looked around. She was bothered by the fact that the other cheerleaders were there and obviously listening. She grabbed Alan by his arm and started to pull him away. "If you're going to be the 'official painter' of this cheerleading squad, we need to talk. In private."

Alan was well aware of what might happen once Heather had him alone in private. It was clear she was raring to fuck him, and she didn't much care about getting caught. So he said, "Fine. Over here, on the other side of the room."

Heather didn't like that, because the other cheerleaders would still be able to see. But the truth was she didn't really have anywhere private to take him in the first place. She was hoping to get him outside and then see where her feminine charms could take her. But she realized she'd have to make do with this.

Once the two of them were standing well out of hearing range of the others, Heather spoke to him quietly. "So... I want my reward. Today."

"Heather, what are you talking about? There is no reward. That'll only happen once you get the FINAL lab results."

"Why are you being such a hard ass about that?" she griped. "Do I need to remind you that I'm the head cheerleader and the most beautiful girl in school?"

"Yeah, and you're also a self-admitted 'naughty, shameless, cock-hungry slut.' Those are the very words you called yourself earlier. Which means who knows who you've been with? I'm not sticking my dick in you until I get the all clear. Period."

She glared at him. "Alan, you're starting to really annoy me. It looks like I need to remind you that you're a social nobody. Harsh, but true. Most girls wouldn't even give you the time of day. And yet, here I am, practically begging-" She cut herself off, because she believed that she never begged anyone for anything. "Well, not begging. Let's say I'm strongly encouraging you to have sex with me. And yet you say no. Do I need to turn the screws on you?"

"I don't know what that means. I'll give you the benefit of the doubt and act like you're not thinking of blackmailing me or some crap like that. That's not going to work with me. Look. It's clear that I'm not like the other guys you've been with. I'm not going to be pushed around. You're right that I'm a 'social nobody,' but that means I have nothing to lose. I don't give a shit about my reputation here. And I couldn't care less about girls not giving me the time of day. That's because I have other lovers outside of school, lovers who are even more beautiful than you are."

She snorted. "Yeah, right. As if that's even possible!"

He rolled his eyes at her hubris. He decided to hype up some mysterious intrigue about himself, to keep her at bay. "There's a lot of things about me you don't know. I keep a very low profile here at school, on purpose. The truth is, I'm quite a player, but I prefer older women, because they've got the voluptuous, busty bodies I like best, and they've got the sexual experience to tear up the bed sheets. A girl like you, well... you're just not all that, in my book."

She pointed at him, practically poking his chest. "Hey! I'll have you know that I'm VERY sexually experienced!"

"Yeah, but not in a good way. Fucking a bunch of sexually clueless teenage boys doesn't help anything. And you're a selfish lover. For instance, your blowjob skills, frankly, are pathetic."

"I can learn! Give me a chance, right here, right now. I can dismiss these other losers no problem. Then you and I can use this room and I'll show you what I can do." She felt insulted and did want to prove her skills to him. But also, she figured that if she could get him to agree to that much, he'd end up fucking her as well before they were done.

He shook his head. "Not gonna happen. I'm not even tempted. You have very little hold over me. I'm not all wowed by the 'great' Heather Morgan." He gave her a dismissive look. "So don't play games. I'll fuck you tomorrow, if you have the right results, and a place to do it."

She was miffed, but her gut instinct made her think he was telling the truth. She decided to back off on pressuring him, at least for now. "Of course I have a place. You're standing in it. How about tomorrow at lunch?"

"We'll see. I highly doubt you'll get the final test results that fast."

"You'll see. Don't worry, I'm on it!"

Alan was able to leave a short time after that. Heather had to be careful not to talk to him too much, given that the other cheerleaders were watching and paying attention.

As Alan unlocked his bike outside the theater room, he thought, Man, I'm really pissed at Heather and her vague threats. If I look up "bitch" in the dictionary, I expect to see her face there! But, I must admit that I'm getting a kick out of "riding the tiger" with her. It's true that I don't have much invested in my social status here at school, so why not? I don't have much to lose if things went sour with her.

Besides, she IS a babe! Of course I had to be harsh with her. No way could I tell her how she thrills me. Maybe I get off on the danger. Man, I've got a major boner right now just from talking to her and seeing her practically beg to give me a blowjob! My life has changed in such a dramatic way that it's totally unreal. Heather wanting ME?! Heh!

He got on his bike and started to ride through open parts of the school grounds. I can't wait to get home. Sis still has her punishment, but Mom will be waiting with her eager mouth. Or even better, her cleavage and mouth! I could go for a titfuck-blowjob combo to take the edge off. Sweet!