6 Times a Day

Extra Long 3.4K words

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When dinner ended, Alan went to the living room to unwind and watch some TV.

But before he found a program to watch, Katherine came in and sat right next to him. "Okay, spill the beans."

"What do you mean?"

"You were trying to avoid me earlier, hoping I wouldn't follow up with the rest of our Heather discussion. But you might as well tell all now, because I'm not going to let you slide on this. Tell me what's going on already!"

He evasively joked, "Okay. 'What's going on already.' There, I told you. Hey, that was easy."

"Ha ha. Now, let's continue where we left off. What exactly have you two done with each other?"

He tried to avoid answering by going on the offensive. "Okay, let's talk. But first, I still don't understand your behavior with her today. I know you said you set up a trap for her, but you could have just seen her at the beach with high heels and moved on. But I saw that you two hung out there for, like, an hour. And yet it looked like you two were actually having FUN together. What gives?"

Katherine frowned. "You're right. It is weird. To be honest, I'm almost as baffled as you are. I told you that I was trying to be nice to her because I was trying to figure out clues about her interest in you, and she was trying to get info out of me. But, to be honest, we talked about other stuff for most of the time. And she was NICE! It's like she wanted to be all buddy-buddy with me!"

He prodded, "And?"

"And that's what happened: we were all palsy-walsy. It was bizarre. She actually was genuinely enjoyable to be with! You saw us there; we were having fun together. I can't deny I had a good time."

"What about her being a bitch? You can't just forget all that if she's suspiciously nice for an hour or two, right?"

"Right. But I figured it wouldn't hurt to get on her good side and kind of play along. I mean, you have NO IDEA how powerful she is at school!"

"I think I do."

"No, you don't! For one thing, you're a guy. Sure, she's good at manipulating guys, especially with her looks, but her power amongst the girls is simply INSANE. Okay? Trust me on this. Besides, I can't stand how she treats us, the rest of her cheerleading squad, every damn school day. I figure if she gets friendly with me, maybe that'll help not only me, but the rest of the squad as well. Like, you should see how she acts around her best friend Simone. She's almost normal with her, and Simone somehow manages to hold Heather's bitchiness down to dealable levels. So I was thinking maybe I could play the Simone role for the squad."

He pondered that. "Okay, I get that much. But what does she want from you? She must have some motive."

"That's obvious. I think she has the hots for you. She figures that if she gets on my good side, that'll help her get on your good side."

"Hmmm." That made sense to him, but he was reluctant to admit it. "So when she was questioning you about me, what did she ask you, exactly? Did you tell her anything I wouldn't want her to know?"

"Nah. It was all getting-to-know-you kind of stuff, pretty much. What kind of music do you like, that kind of thing. I'm no dummy. I'm not going to give away any of our big secrets."

Her tone suddenly got more aggressive. "Now that you had your turn asking questions, it's my turn. I have some questions for you, buster! Have you or have you not gotten intimate with her?!"

He squirmed under her scrutiny. "Um..."

She pressed him, "The clues are there. The things she was saying to you, that was not beginning flirting; that was advanced flirting. Like, grad-school advanced! All this talk about 'cramming' and wanting to 'get a ride' from you, and trying to 'work you in.' I mean, come on! That's seriously blatant. What's up with THAT?!"

He pondered that question, and couldn't find a way out. Then finally he said, "Sis, I cannot lie to you. So... I'm gonna take the fifth."

"WHAAAAAT? Brooooother!" She shook her fist at him. She wasn't really going to hit him, but it was the kind of body language she used with him at times of great frustration.

He chuckled a bit at her angry fist gesture. "Sis, you crack me up."

"Come on! You gotta give me more than that! Are we best friends or what?!"

"We are."

"Plus, I'm your fuck toy and one of your personal cocksuckers. Doesn't that entitle me to at least a few clues about who else is polishing your fat knob?!"

"Okay, I'll tell you a little bit. Out of the blue, a few days ago, I ran into Heather after school. She kind of acted all interested in me. Things happened."

"'Things happened?' Care to clarify?!"

"No. I don't kiss and tell."

"A-ha! So there was kissing!"

"Maybe."

"GRRRR!"

He pleaded, "Seriously, now that I seem to have fallen into this lifestyle of having multiple lovers, I have to be super careful about not kissing and telling, or I could get into hot water fast. Can you please try to cut me some slack on that?"

"A-ha again! You all but called her a lover."

"No I didn't. 'Things happened.' That's all I can say. Maybe it was just heavy flirting, or a simple kiss. It could be anything." Trying to deflect her prying, he said, "It's weird. I mean, why would SHE be interested in ME? I've been thinking about it. The panty-painting thing doesn't explain it, not by itself. My theory is that Kim talked to her about me and hyped me up."

Katherine's eyes lit up with recognition. "A-ha! THAT makes sense. Now I get it. Kim is sky high over you, so I could totally see that. Oh, shit! That's not good! I'm gonna have to talk to Kim before she does any more damage."

Alan nodded. Although he'd enjoyed fucking Heather, he didn't want to be blindsided like that again. Besides, he already had more beautiful women in his life than he could handle.

He added, "It's possible Amy said something to her too."

"Oh shit!" Katherine was lost in thought for long moments. Finally, she said, "Since you've kinda told me some secrets here, I have a secret too. 'Things happened' between Heather and me too."

"What?! Really?! No way!"

Katherine nodded. "Yeah. I kind of felt obliged to as part of having to cover up the whole painted-panties thing. It's a long story. But it was a totally casual-sex kind of thing. Nothing serious. In fact, when I hung out with her earlier today, it was like it had never happened."

He asked, "Do you have any idea how amazingly sexy that is? Geez! I can totally picture you two getting it on!"

Katherine rolled her eyes. "Guys. What's up with guys watching lesbian sex? So predictable." But she was secretly pleased. She figured anything that made her more arousing in his eyes was a plus, especially since she had to compete against the likes of Susan and Suzanne, and now maybe Heather, for his attention.

She went on to explain a lot more about the secret politics and personality conflicts amongst the cheerleading squad.

It was a real eye-opener for Alan. He found himself even more awed by Heather's power and the way she used it.

Later that evening, Suzanne and Amy came over to the Plummer house after dinner. The plan was for everyone to watch TV or a video together.

The whole gang sat down in the living room: Alan, Susan, Suzanne, Katherine, and Amy. The women weren't dressed in any particularly sexy manner, but they all were so gorgeous that Alan's dick got erect in a matter of minutes just the same.

Amy was the first to notice. She pointed at his crotch. "Oooh! Look! Check out Alan's thingy; it's all hard and stiff!"

That made everyone uncomfortable, especially since Amy was the one who'd said it.

A particularly displeased Suzanne said, "Um, Honey Pie, about that. You see..."

Before she could get far, Amy said, "Chill, Mom. Don't worry; I know what's going on. Alan's getting a lot of help, so his thingy doesn't stay all stiff and hurt-y. Don't mind me. I'm just gonna pick out something to watch while you work out who helps him this time."

Suzanne squirmed uncomfortably. "Um, it's not exactly like that..."

But Katherine said, "It IS exactly like that. Aunt Suzy, Amy is a big girl. She's here so much, how could she not figure out what's happening? And she has an excellent question: Who is going to help him this time? Or are we just going to leave him like THAT?"

All eyes went to Alan's crotch again, except for Amy who seemed very busy looking over the DVD collection.

He crossed his legs, but there was no hiding the fact that he was sporting a big boner. He glanced around, noting all the hungry looks. If his dick hadn't already been erect, it would have become so just from seeing the way that Katherine, Susan, and Suzanne were each licking their lips as they stared at his crotch.

An uncomfortable silence seemed to stretch into eternity. It was clear that all three of the women wanted to help, but there was no established procedure for this kind of situation.

Alan thought, Shit! What to do, what to do, what to do? I need to say something fast before things get even more weird. But who do I pick? Hmmm. Not Mom, since she just helped a little while ago. Probably not Sis either. After all, Mom still has issues with her helping, and I don't want to push her on that. What about Aunt Suzy? I suppose she's still "in the doghouse" from what happened in her backyard the other day, but Mom seems to have forgotten about that. This would be a good test to see if Mom has really let her off the hook.

So he said, "Um, since Mom helped me out a little while ago, and I know Sis is still being grounded and all, I guess that leaves you, Aunt Suzy. Would you mind helping me with, well, you know... Doing my thing?"

Suzanne smiled and stood up. "Not at all. Shall we?" She nodded towards the stairs.

Alan got up and took her hand. The situation was awkward, but also very exciting. The fact that everyone knew exactly what was going to happen, even Amy, was major. He had visions of this kind of thing happening a lot from now on. He said, "Why don't you guys watch whatever? Don't wait for us. I'm sure Aunt Suzy and I won't be gone long, and we'll be able to catch up."

The mood remained awkward after Alan and Suzanne had left. Both Katherine and Susan were lost in thought, mulling over their missed opportunity.

But Amy quickly broke the mood by suggesting, "Hey, if it's just us girls picking, we should go for a rom-com. Something cheeseariffic!"

Susan tried to focus on the movie suggestion, rather than on the joys of slobbering all of her son's thick shaft. She frowned in confusion. "'Rom-com?'"

Katherine explained, "Romantic comedy. I think that's a good idea. And before you ask, 'cheeseariffic' I assume means something really cheesy. You know, over the top. Right, Amy?"

"Right!"

Meanwhile, Suzanne stopped in the front foyer to put on a pair of high heels. She'd been relaxing in bare feet in anticipation of watching a movie, but high heels were becoming an integral part of the cock-pleasuring experience. She also slipped on a pair of panties while he wasn't looking.

As Alan walked hand in hand up the stairs and out of hearing range of the others, he said, "Well... that was weird."

Suzanne replied, "I know what you mean, but what could we do? It's like Angel said: Amy is there, and there's no easy way to get around her finding out certain things. I'm need to have a talk with her about all this, soon."

Alan realized that Suzanne misunderstood. He'd been talking about the entire situation, and she was thinking just about Amy. He decided not to say anything more, figuring he'd probably only mess things up.

As soon as they reached his room, Suzanne said, "Now, go sit on the edge of the bed and think about what you want to do first."

He crossed the room while she lingered near the door. "Um, okay. But aren't you going to close the door?"

She gave a naughty smile as she looked back to the door. She'd closed it most of the way, but left it open an inch or two. "Oopsies! I might have forgotten to close it all the way. I sure hope no sexy, busty mommy types come upstairs and take advantage by listening and peeking in." She winked knowingly at him.

His eyes bugged out. "Man! Really?! But what if Sis comes by instead?"

"Mmmm... Sounds like fun! Just be mindful of what you say, keeping in mind that one of them might hear, okay?" She started to sway slowly as she unbuttoned her blouse, even though there was no music playing.

"Hey, what are you doing?"

"What does it look like? A striptease." She leaned over, showing off her huge tits as they swelled forward in her mostly unbuttoned blouse.

"You know I love it, but it's really not necessary. I mean, I'm as hard as I can get!" He realized there was no reason to keep his clothes on, so he quickly shucked off his shorts to illustrate just how erect his dick was.

"Ooooh! Yummy!" She kept on swaying as she unbuttoned her blouse all the way, freeing her tits. "As far as necessary, let me be the judge of that."

He admitted, "The thing is, I feel kinda bad. I mean, you're doing all this amazing stuff for me, and what do I do in return? It's not fair."

"Fair? You let me decide what's fair. The fact is, I consider myself the big winner here. After all, you chose me. The fact that there are three of us eager to help you and only one of you means you've gotta redefine your meaning of fair."

He wanted to argue against that but his brain wasn't working very well; all he could do was gawk at Suzanne's perfect body. But as the silent striptease continued, he blurted out the first thought that popped into his head: "Hey! You're wearing panties!"

She turned around, showing off her fine ass as she slid the panties down it. At the same time she teased, "I am? Are you sure?"

His head pounded wildly but still he managed to reply, "Sure? Sure, I'm sure! I can totally see them!"

She chuckled, pleased at how frazzled she'd gotten him already. "Okay, you got me." She suddenly turned around to face him.

"Oh fuck!" he gasped in awe as her big globes jiggled around, swaying, and her dark brown bush came into view.

She bent over, pulling the panties down to her knees. That also naturally set her heavy but firm tits dangling. "See anything you like? Anything you'd like to... fuck?"

He gasped again. It was too arousing. He couldn't help but start stroking his exposed erection, even though he knew he wasn't supposed to do that.

As she pulled the panties down to her feet she said, "By the way, you're right, I am wearing panties. Or at least I was." She tossed them away and stood back up. "I know that's against the house rules, so you're probably gonna have to spank me. But would it help my case if I say that I just put them on a few minutes ago, solely so I'd be able to take them off when we got upstairs?"

He stared wide-eyed at her nude body. He was too horny to speak. He was stroking his erection faster and faster.

She belatedly realized that her striptease was too effective. He was so worked up that he was liable to masturbate himself to orgasm if she didn't act quickly. She crossed the room to kneel between his legs. "So... what did you choose?"

He couldn't remember off hand what her question was about, so he was going to ask her to repeat it. But as soon as her fingers closed around his shaft, he forgot what to say. Then she started stroking, and he even forgot her last question. Partly it was the physical pleasure, but he also just adored the sight of her perfect face and the impossibly curvy, naked body below him.

She chuckled a little, then snapped her fingers. "Sweetie? Your choice, remember? How do you want to do me?"

He grinned as an idea came to him. "How 'bout a sixty-nine?"

"You know better than to ask for something that's against the house rules, like a sixty-nine. Your choices are handjob, blowjob, and titfuck."

"Oh man! Hard decisions. I wonder what a handjob would feel like."

She snickered, since she knew as well as he did that she was in the middle of one.

He continued to ponder. "Hmmm. Tough call. I would say titfuck since that's pretty new and your tits are out of this world, but then I think about your extra-long tongue and all the things you can do with it, not to mention your sweet lips..."

"You mean this tongue?" She leaned forward and licked circles around his cockhead while her hands continued to steadily pump up and down.

"Oh! MAN! SWEET!"

She chuckled some more. "Hmmm. I doubt we're gonna get much more out of you since you're so lost in the moment. Since you can't decide, I guess I'll just have to do both at once."

She scooted up and encased his erection in her deep cleavage. Then she tilted her head downward and managed to lick all over his cockhead. At times she barely managed to reach his sweet spot with the tip of her tongue, but it was such a difficult effort that she couldn't do much with it. She was frustrated because she was so close yet so far away.

She made up for that by alternating between focusing on cocksucking and bobbing down his shaft, and pulling back for a licking and titfucking combo.

He didn't care much about what she was doing, because he knew that whatever it was, it would be heavenly. He felt like he was raging drunk, but drunk on lust.

Suzanne knew how to keep him maxed out on pleasure, while being careful that he didn't go over the edge and cum. In addition to wanting to prolong the experience just as much as he wanted to, she figured that if they took a long time, eventually someone would come by to see what was taking them so long. She hoped that would be Susan, and that the experience would further weaken her sexual resistance.

As a result, the naked redhead spent over half an hour licking and sucking every possible way, as well as sliding her hefty melons all over his shaft.

She also practiced deep throating again. Even though this was only her second attempt on him, the improvement was substantial. She still gagged a little bit, and she couldn't stay down all the way for very long, but this time it provided Alan with great pleasure. Her throat squeezed his cockhead so tightly it was like he was sliding in and out of a cunt. On top of that, her long tongue would roam against the remainder of his shaft. She even experimented with a few things, like repeatedly gulping while he was in her throat, which would momentarily and unexpectedly tighten the pressure against his dick.

Additionally, she had taken to heart his complaint from when he thought he was talking to Elle, that she didn't let him touch her enough. So she let him explore her tits and ass whenever he took one of his strategic breaks.

Alan was beginning to understand that cumming six times a day, every day, was a hell of a lot of times. And not only that, but the quality of those times was simply off the charts. He felt like he'd experienced more ecstasy and arousal in the last week than in his entire previous year of masturbating, and he was pretty sure he was right.