6 Times a Day

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William Osborne

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When school let out, Katherine left immediately to go clothes shopping, looking in particular for ‘catty’ items like those with leopard skins or tiger stripes. She hoped she could talk some of the others in the family four into going to a sex shop later on so she could pick up even more outrageous items. This left Amy by herself as she bicycled home.

Amy was very distraught by what she’d learned of Alan’s near disasters. She hurried back to the Pestridge home, dumped her bicycle in the garage in haste, and rushed inside. “Mother! Mother! Mother!” she yelled as she burst into the house from the garage. She made a point to refer to Suzanne as ‘mother’ and not ‘mom’ anymore, since that term was now reserved for Susan.

Suzanne was upstairs in the family den, typing away on the computer. As Amy bounded up the stairs taking two at a time, Suzanne idly replied in a loud voice, “Yes, Honey Pie? I’m in the den.” More often than not, Amy’s great excitements turned out to be minor matters, so she wasn’t terribly concerned about this latest supposed crisis.

But Amy ran right up to her, practically breathless, and gave her a very worried look. “Mother! It’s Alan! It’s serious. He’s hurt!”

All the air rushed out of Suzanne’s lungs and she nearly fell out of her office chair in a faint. “My Sweetie?! No! Where?! Is it bad?”

“In the knee! AND the elbow! It was so bad he bled for a while and everything! We’re talking a serious scrape!”

Suzanne felt a great relief, followed by a desire to soundly box her daughter’s ears. “Amy! Is that all? You nearly gave me a heart attack. Well, at least you have my full attention, that’s for sure. Start from the beginning and tell me everything.”

So Amy told Suzanne all she knew about the painted chair incident and the stairway “accident.” She told the whole thing breathlessly, as if she’d never recovered from running up the stairs.

When she was done, Suzanne said in a calm voice, “Now, Amy, my Honey Pie. Really, it’s not that bad. We know Alan, don’t we, and he knows how to handle these kinds of things. I’m sure he’s going to teach these bullies a lesson or two.”

“But Mother! You should see how big these thugs are. They’re gigantomonstrously huge! Don’t you remember his black eye from last week? Think what these guys could do to him. They could break even a strong guy like him, just like a twig! And there’s all these rumors everywhere about Alan, and they’re not good, and they’re all my fault! I talked too much about how he fucks all the girls so good, and now everyone is so jealous. It’s like the whole school wants to take him down a notch. We have to fix it. You have to use your special powers!”

Suzanne laughed. “My special powers? Don’t you remember? It was Susan who wore the Wonder Woman outfit at the last costume party.”

“No, silly, I mean your scheme-y powers. Do your scheme-y thing and make it all better.”

Suzanne chuckled some more, pleased at how much faith Amy had in her abilities, and how much she cared for her boyfriend. “Sorry, my darling, but I don’t know the first thing about all the high school dynamics and intrigues. Proper scheming requires a lot of information and preparation, and without that I’d probably only make things worse. But don’t worry. You can help him all you can, if you get the chance, but you should trust that he’s going to come out on top.” Suzanne smiled dreamily. “He always does, if you know what I mean.”

“Yeah…” Amy said, suddenly a bit dreamy eyed herself. The “on top” comment caused both of them to start thinking about Alan’s sexual prowess. They were both so easily turned on by Alan by now that it didn’t take much to get their nipples hard. Even a little comment like that could do it.

But then Amy got excited and breathless all over again. “Oooh! That reminds me! Guess what he told me, just after he told Sis and me about all that bad stuff, right as he was walking away?”

“What?”

“He said tonight is the night for you and me, together! Can you believe it?! Last night he took my ass, and tonight he’s going to watch while you and I are going to go all the way for the first time! Does life get any better than that, or what?”

Suzanne smiled, calm serenity personified. “Nope. It doesn’t.”

Amy looked at her mother curiously. “Mother, what’s wrong with you? How come you’re not all excited?”

“Well, for one thing, you’ve forgotten the Golden Rule: no one talks about anything sexual in this house, no one does anything sexual in this house, and in fact, no one even thinks anything sexual in this house. I don’t care if Brad and Eric are both gone for the whole afternoon, we have to be consistent about that, because you just never know.”

“M’kay, Mother,” Amy said, dropping her head. “Except that I’m thinking something sexual this very moment. I’m thinking about you, and what we’re going to do to each other tonight.” She looked up into her mother’s green eyes, a bit more excited. “And since I just told you that, that means I’m talking about something sexual, too. And I’m even doing something sexual. I’m so bad!”

“You are? Doing what? Where?”

Amy was standing right in front of Suzanne, who had swiveled her computer chair to face her. Now Amy lifted up a leg, moved her foot underneath Suzanne’s skirt, and then placed her foot on top of Suzanne’s pussy. She began rubbing her foot up and down the silky panties covering Suzanne’s crotch. She did all this in a matter of seconds, then once she started the rubbing, she said in a deadpan voice, “I’m doing this.”

Suzanne laughed again. “Very cute. But please stop. This is our house. The Pestridge house! Sex here is totally taboo!”

Amy continued to rub her mother’s crotch with her foot. “Even sex with your own husband?”

Suzanne laughed yet again, although scornfully this time. “Especially sex with Eric! You know that. I don’t even let him kiss me anymore. I’m Alan’s woman now, just like you and everyone else, I might add. But even talking about these things here is completely forbidden. What if Eric has gotten suspicious and has been bugging the house, for instance? Amy, what’s gotten into you?”

“You’ve gotten into me, Mother, or at least you will be getting into me tonight. I’m so excited that I’m gonna burst! And as for doing it here, aren’t forbidden things the funnest? Like fucking Alan, your own son? Or even your own real flesh and blood daughter, little ol’ Amy?”

As Amy said this, she pressed hard with her big toe into Suzanne’s pussy lips, causing the panty fabric to give. Her big toe penetrated the entrance to her mother’s vagina, which brought a shocked expression to Suzanne’s face. Amy began making little strokes and wiggles with her toe, a move that was surprisingly effective, given the inherent limitations of what toes can do.

Suzanne cried out, suddenly distressed, “No! Amy, no! Not the cunt! Please, anywhere but the cunt!”

But Amy didn’t stop her toe-fucking or say anything.

So Suzanne added in a near-whisper, “You know the problem with my cunt.”

Amy giggled mischievously. “No, I don’t. Uh-oh. Don’t tell me you have one of those nasty yeast infection thingies. Here, let me make it better with my toe.” She giggled some more as she kept wiggling her toes.

Suzanne groaned with frustration and lust. “No! Amy, you… meanie! I was almost going to call you a worse name, because I’ve never seen you like this. I’m trying to do some important things here. What’s gotten into you? You’ve always been so obedient.”

“Actually, I think the question is: what’s gotten into you? Uh-oh. Looks like I’ve put my foot in my mouth… or somewhere. I think I’ve gotten off on the wrong foot, hee-hee. Or maybe you’re getting off on my right foot!” She giggled hard with this last comment, especially since her right foot was indeed pressing ever deeper into Suzanne’s pussy. Her entire big toe was now swallowed up in Suzanne’s nether hole.

Suzanne, too, couldn’t help but chuckle a bit. “Okay, very cute… but stop! You know the problem with my cunt: it rules my brain. Once my cunt gets excited, I abdicate all responsibility, and who knows what will happen after that? Do you want to save all the best stuff for when Alan is watching tonight, or are we going to do it all with each other right here and now?”

Amy suddenly frowned, and made a tiny, “Oh.” She quickly removed her foot.

“Phew! That’s a relief!” Suzanne collapsed with a sigh. She readjusted her skirt, covering up her crotch in the process. “Honey Pie, believe you me, I’m just as excited about the promise of tonight as you are. God, it’s been a long time coming. But long ago I learned about something called patience. Tonight will arrive soon enough. In the meantime, savor the anticipation. Dreaming about what will come is half the fun. Okay?”

“M’kay,” Amy replied forlornly. She rubbed her toe into the carpet bashfully. “But I’m not good with the whole waiting thing. When I get all nervous and ‘fraidy, I just wanna suck on Beau’s cock to relax. But he’s not around! He went off to another stupid SA-Club orgy without me.”

“You know that’s his right and privilege,” Suzanne pointed out. “He’s been very up front about it. That’s the price we all pay for being in love with a man who’s earned himself a harem. We have to wait our turns.”

“I know, I know. But it’s still a bummer. I thought that if you and I played around a little bit, I’d feel better. Can’t we at least make out? Just a teeny weeny French kiss and tit grope?”

Suzanne’s chuckled. “Sorry, my love. Once we get started with something like that, we won’t be able to stop. Things have been building up between us for a long time, and now it’s all about to explode. If you would have tried that toe stunt of yours at the Plummer house, I would have completely lost it, for sure. Let’s not blow it when we’re so close. Just let a few hours go by. Do some homework for once. Maybe think up ways to get back at those football players. I can help you with that later this afternoon, if you promise no touching.”

“Cool! Mother, if I could help him beat those thugs, he’d be so proud of me! Proud of us! Even though we’re all family now, you and I will always be a special team, right?”

“Right. That reminds me. I have some interesting news on the divorce front. Good news.”

Amy’s eyes went wide. “Oooh! Super awesomeness! Who’s divorce, yours or Susan’s?”

Suzanne smiled like the Mona Lisa. “You’ll just have to wait until tonight to find that out, too.”

“Grrr! Mother, you’re so mean! How am I going to make it? That’s hours and hours and hours away!”

“Well, we may not be allowed to touch until tonight, but I’ll bet Susan or Katherine wouldn’t mind a friendly hello. Maybe both of them together, even. I’ll bet Susan’s breasts are swelling up to an obscene size, waiting for someone to suck all the milk out of them.”

Amy’s eyes went even wider.

Suzanne added, “Too bad she doesn’t have any considerate daughters to help out…”

“I’m outta here!” Amy yelled back at Suzanne, because she was already out of the den and leaping down the stairs in a flash. “I’ll be back for the football scheming. Can’t wait till tonight! Later!” By the time she got to “later,” she was already out the front door, which she then slammed behind her.

Suzanne just chuckled and shook her head like the amused and chagrined parent she was. She strongly considered masturbating herself to thoughts of her daughter, but she remembered that she had some urgent and important things to do. She went back to her computer screen, which was filled with legalese about divorce law.

Alan and Sean met at the bicycle rack and biked to Kim’s house together. Alan had already explained to Sean much, though not all, of what they would see and do that afternoon. He told him more about the S-Club as they biked there. He joked, “Some call it the SA-Club, which can mean the Service Alan Club, but on a day like this it’ll also mean the Sean Action Club. Don’t worry, you’re going to have a hell of a lot of fun.”

Sean gulped nervously. Mere days ago he’d been a complete virgin. Things were moving too fast for him. “Christ, you’re kidding me. The Service Alan Club?! How the hell am I supposed to compete with that?”

“Relax, it’s just a jokey name. They don’t mean anything by it.” Alan knew that wasn’t true, but he wanted to put Sean at ease. “Besides, sex is so easy. Before I started I thought it was this really complicated thing, and sure, you can spend time learning advanced techniques, but the basics come completely naturally. And that’s all you need.” That wasn’t entirely true either, but he figured it was close enough.

“Thanks, dude. I hope so. I’m really nervous.”

Alan patted him on the back. “Chill. You’ll be awesome.”

Kim met them at the door to her house, but they didn’t dawdle with pleasantries. The three of them walked straight up to Kim’s bedroom, and then Kim went off to get some things.

Alan still saw concern in Sean’s eyes, and understood it. For one thing, he’d told his friend to expect to be severely tested today. For another, he’d told him that he’d probably end up fucking a number of girls today, perhaps even experiencing more than one girl at a time. That was a lot for a self-confessed complete nerd to take, especially one who still strived to maintain some kind of loyalty to his one true love, Heather.

Alan knew exactly what Sean needed to hear, and told him, “Don’t worry. Remember, you’re doing this for Heather.”

Sean sighed heavily and said, “I know. I’ve been thinking a lot about that. It’s like Heather is a fallen angel, an innocent girl trapped in a whorehouse. I have to come in there and rescue her. But the only way in is to pretend to be a customer: just another John. I’ll have to treat her like dirt and act like an uncaring John at first, as I slowly gain her trust.”

“Exactly!” Alan agreed as he sat down on Kim’s bed. “Excellent metaphor. Better than the sci-fi ones we’ve been coming up with lately. And like a John, you’ve got to have sex with some other whores and see her have sex with some other Johns as part of this undercover operation. That’s what happens in a whorehouse.”

Just then, Kim walked back in, carrying some rope and a piece of cloth. She smiled but said, “Hey, who are you calling a whore?” ｂ𝚍ｎｏ𝚟ｌ.

“Certainly not you,” Alan said very sincerely, but at the same time he unzipped his shorts, flopplng out a very erect dick. “If you were a whore, I’d have to actually pay you to suck my cock.” However, he winked and said this good-naturedly. There was a certain inherent goodness about him that allowed him to get away with an outrageous joke like that.

“Bastard,” Kim complained as she stuck out her tongue playfully. Then she dropped to her knees in front of him and began to eagerly suck him off.

Sean, sitting next to Alan, looked over in complete shock. “H-how…? How did you do that? You say this cutting, degrading thing, and then she drops to her knees to blow you. I don’t get it. If I were to try something like that, I’d get slapped, big time! That kind of thing doesn’t happen in real life, does it?”

“I know what you mean,” Alan agreed. “It’s all in how you do it. I’ve stumbled on to the fact that a lot of women love a guy who’s domineering, yet still has true love and affection for them that can’t be faked. It’s all about knowing when to be naughty and when to be nice. Everyone likes some naughty stuff from time to time, if they’re really honest with themselves, and that doesn’t make them a lesser person. Keep that in mind when you watch me fucking Heather in a few minutes.”

“WHAT?!” Sean stood up, instantly defensive of his dream girl. “You can’t be serious!”

“I am,” Alan replied, still calmly sitting there and showing no sign that Kim was fervently sucking his dick. “Remember what I said about you being on the fast track? This is the very fast track. You’re never going to get it right until you see with your own eyes exactly what she likes. But when you see me calling her all kinds of rude names and treating her like a whore, remember that there’s love and affection there. I’m giving her what she really wants. I’m doing all I can to make her happy. Sometimes it’s funny what makes a girl happy. You’d be surprised and delighted.”

He looked down at his crotch as he continued, “Take a look at Kim here. Even though she doesn’t really like guys or want a boyfriend, she absolutely loves sucking cock. All I have to do is flop out my dick and lean back, and she’s happy to slurp and lick me all afternoon. Isn’t that right, Kim?”

Kim sexily moaned a hearty affirmative, with Alan’s cockhead tickling her tonsils. She was trying to deep throat him, as it was something she’d been reading and thinking about, plus she figured the less Sean saw of Alan’s penis at that moment the less traumatized he’d be. She was unable to get past her gag reflex, but she nonetheless was getting a great deal of Alan’s shaft in her throat.

Sean said with growing exasperation, “But… You’re just sitting here talking to me like she’s doing nothing. How… What’s… How do you DO that?!”

“You think it’s easy?” Alan asked, while still sounding as calm as could be. “It’s not easy. I’m feeling an incredible amount of pleasure right now, thanks to Kim’s busy tongue and lips. But you have to know your lovers. I’ve noticed that the more I ignore Kim, the harder she tries to please me. Right now, she’s so determined to get me to blow or at least moan loudly that she barely even knows if she’s cumming or going herself. Right, Kim?”

Despite her condition with his stiff rod filling her mouth, she managed to joke with a muffled shout, “Cumming!”

Caressing Kim’s silky soft hair with one hand, Alan continued, “In fact, Kim is so hungry to suck cock, as you probably know first-hand from your own training sessions with her, that I could treat her any way I liked and she’d still come crawling on her knees for more. But she’d do it despite that rude treatment, not because of it. So I wouldn’t do that to her. Whereas with Heather, it’s the opposite. She’ll hardly get aroused unless I call her a bitch and a slut, and that’s just for starters. So I treat them differently.”

Sean backed away in amazement and even horror. “Dude, I know what you mean. On one level, an intellectual level, I get it. Kinda. But I can’t see it with my own eyes! Heather. You, doing Heather! Shit! And calling her names?! Give me some time to adjust!”

“I am.”

“Wait. You’re actually sticking your dick in Heather’s vagina. Like, in it, and everything!”

Alan grinned at Sean’s incredulity. “Yes.”

“My GOD! Like… IN her body! Your dick is gonna go in… inside… her!”

“That’s generally how it’s done,” Alan deadpanned. “Why is that so hard to believe?”

“She’s Heather! Heather fucking Morgan! She’s like royalty! And you, well, no offense, but you’re just you. Shit!” He was pacing back and forth now, almost completely forgetting about the blowjob taking place in front of him due to his nervousness. “Is she gonna be here? Soon?!”

“Yes. Deal with it.” Alan felt strangely calm, but also unusually relentless. He knew he had to shock Sean into accepting the new reality. “I know it’ll be difficult. That’s why we have the rope here, and a gag for your mouth. My plan is to put you in the closet over there, and you’ll watch me do Heather through the slats of the closet door without her knowing. That way, you don’t have to worry about yelling or anything. We’ll put some music on to cover any noise you might make, too. If it gets too much, just close your eyes. Kim is supposed to tie your arms behind your back, but she’s a bit preoccupied, so come closer and I’ll do it. You were just telling me on the bike ride over how you’re a man, how you can handle anything. So prove it! This is your big test.”

Sean paced back and forth, still trying not to look at Kim’s bobbing head in Alan’s lap. He was amazed how unfazed Alan was about the blowjob, but he felt too awkward to discuss it. “I don’t know, dude. I don’t know. Can’t you do it with another girl first, as like a Heather stand-in? It’s shocking enough just to see another guy have sex. And you’re my best friend. I don’t want to see you like that. That’s freaky!”

“No, it’s got to be Heather. I don’t treat anyone else… anyone… the way I treat her, and you have to learn Heather’s true sexual nature if you’re to stand even a ghost of a chance with her. But don’t worry, you’re going to be shocked, but you’re also going to enjoy yourself. I have a surprise or two for you.”

Alan laughed at that, but Sean couldn’t figure out why.

So, a few minutes later, Sean found himself in the bedroom closet, with his arms tied behind his back and a cloth stuffed in his mouth and tied around his head. The closet was stuffed to the brim with clothes on hangers, so he found himself in a narrow space between the clothes pressing against his back and sides and the slats of the door just a few inches from his face. The bed had been moved right up to the closet so he could have a better view, based on the downward angle of the slats. The repositioned bed also trapped him in the closet, since the closet doors opened out and now they couldn’t be opened.