Six Times A Day - Cover

Six Times A Day

Copyright© 2004 - 2015 by Spacer X. All rights reserved

Part 65: Tonight's the Night

Harem Incest Sex Story: Part 65: Tonight's the Night - High school senior Alan is diagnosed with a rare condition requiring six orgasms a day. The women in his life - mother, sister, neighbors, cheerleaders, and more - end up swept away by their own lusts while helping him. This epic roller coaster of passion, love, and sex leads to results no one sees coming. The variety of characters, humor, and hot sex will leave you wanting more.

Caution: This Harem Incest Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   mt/Fa   Fa/Fa   ft/ft   Fa/ft   Mult   Consensual   Reluctant   Romantic   BiSexual   Humor   Incest   Mother   Son   Brother   Sister   Daughter   Group Sex   Harem   Polygamy/Polyamory   Anal Sex   Exhibitionism   First   Lactation   Oral Sex   Sex Toys   Voyeurism   Big Breasts   Doctor/Nurse   Size   Slow   Illustrated   mother helps son relieve his blue balls,mother sucks son,mother fucks son,sister fucks her own brother,sister tricks brother into sex

Day 62: Saturday, November 16

Chapter 1

About an hour after Suzanne and Alan left to go "computer shopping," Amy came over to the Plummer house. She learned from Susan that Alan was gone, so she went looking for Katherine, so she could hang out with her best friend.

She found Katherine suntanning on the sun deck on the second floor. Katherine was lying on a lounge chair completely naked except for dark sunglasses.

As soon as Amy walked out onto the sun deck and saw that, she cheered. "Yeay! Nudity!"

Katherine Amy

Katherine had her eyes closed, but she opened them and turned her head to find Amy. She grinned, because Amy was already in the process of taking off her clothes, as expected. She said in a friendly tone, "Hey, Aims, what's up?"

"Oh, not much. It's a bummer Alan's gone all afternoon, from what I hear. Susan was just telling me. But I figured, hey, that sounds like great 'checking for bumps' time, if you know what I mean." She winked and smiled knowingly.

"I do."

Amy was already buck naked, and in the process of pulling another lounge chair next to Katherine's. She had to dust it off as well, because it hadn't been used in a while. As she did that, she asked, "By the way, what are you doing up here instead of down there?" She pointed towards the backyard pool area that the sun deck overlooked. She didn't have to add that the sun deck was very rarely used, since the pool area had several advantages over it, including the pool itself.

Katherine shrugged as she watched Amy settle into her lounge chair. "Oh, I don't know. It's a nice view from here, and it's closer to my room. But I guess the main reason is that I wanted more privacy."

Amy sat up with a start. "Oh? Am I bothering you? I'd better go then!"

Katherine reached out and held Amy's hand. "Don't even think of it! For you I'll definitely make an exception. It's one thing to feel like Mom is staring at me from the kitchen half the time. It's quite another to hang out with my BFF!" She smiled widely.

Amy beamed, since she understood "BFF" stood for "best friends forever." Their lounge chairs were close enough that she was able to lean over and briefly peck Katherine on the lips. Then she settled back in her chair.

The two of them chatted about inconsequential things for a while. Sensing that Katherine was feeling lazy, Amy picked up Katherine's suntan lotion and applied it all over her body. (Unlike Katherine, and due to the fairness of her skin, Amy was more interested in avoiding a sunburn than getting a suntan.)

After a while, when conversation seemingly petered out, Amy spoke up. "Uh, Kat? Can I ask you a kinda personal question?"

"Sure."

"What's it like?" After a long pause, she shyly added, "You know ... getting fucked by Alan?"

Katherine turned to look into Amy's eyes. "Why are you asking me that? I've told you in great detail already, multiple times, as recently as yesterday! In fact, we even talked about it well before he got his diagnosis, months and months ago. Do you remember that?"

"Of course! How could I forget?" In truth, Katherine and Amy hadn't exactly talked about what it felt like to be fucked by Alan back then, but they did discuss how he would be the "perfect boyfriend" if he wasn't already considered family for both of them. Eventually, they even mutually confessed to each other about having some "impure thoughts" about him. But, back then, both of them were unwilling to fully confess their true feelings about him to the other, so they had each acted as if they were bothered by such things.

Katherine asked, "Then what do you want me to say?"

Amy squirmed unhappily. "I don't know. I just ... well, it's kinda on my mind a lot. I mean, like a super duper way lot! 'Cos now that I'm his official girlfriend and everything, and since we're not technically related, there's absolutely nothing stopping him from fucking me. I want it, he wants it, so it's totally gonna happen! And SOON! Right?"

"Right. But we've been over that too in the last day or two. What is it you want me to tell you?"

"I don't know. Just ... reassurance, I guess. I mean ... to be honest ... well, I'm kind of scared. Am I going to be up to snuff, for one thing. That's the main thing, actually. You say it's totally easy, and that the body knows exactly what to do, but what if I freeze up or something? I'm kinda sorta feeling a lot of pressure, especially with this 'Official Girlfriend' title. I've gotta live up to that."

Katherine reached out and held Amy's hand. "You'll do great, I'm sure. Heck, I guarantee it. If anything, there will be more pressure on him than you. After all, guys often ejaculate prematurely. Whereas if you cum early, that's like an extra bonus, 'cos that makes it easier for you to come again!"

Amy smiled at that, but only wanly. "I know, but still. It's the competition thing that worries me the most. Being 'just okay' isn't good enough. He's fucked you a bunch, and you and him have, like, a super special connection. And if he hasn't fucked my mom yet, he will soon, and I don't have to tell you what a ridiculously super sultry sex goddess she is! In fact, I totally bet dollars to donuts that they're fucking right now!"

Katherine sat up in surprise. "Really?! What makes you think that?"

Amy rolled her eyes. "Susan said he's off helping Mom shop for computers. Give me a break. For one thing, she hasn't said word one to me about needing a new computer. For another, she knows as much or more about computers than he does. But the kicker is, if you were her and you got the chance to spend the whole afternoon with him alone and out of the house, what would you do - go shopping or have sexy fun?"

Katherine sat up even higher and stiffer as her alarm grew. "That's a no-brainer. Sexy fun, obviously."

Amy nodded grimly. "So I've gotta compete with my own sex-vixen mother! And not only that, but what about all the others? The only one I can say he's fucked for 100 percent sure is Kim. But there's a whole bunch of maybes, women he's involved with where it's just a matter of time." She counted them on her fingers. "Heather, Akami, Janice, Joy, Brenda, Glor- uh!" She tried to stop herself, but too late.

Katherine practically leapt out of her lounge chair in surprise. "Wait! What?! Did you start to say 'Glory?!'"

Amy had a look that suggested she was totally busted. "Um, no! I was starting to say ... uh... 'glowing.'"

"'Glowing?!' Why the heck would you say glowing?!"

Amy was trying to get out of her fix, but she couldn't think of any plausible word or name that started with a "glo-" sound. And she didn't have any plausible reason to say "glowing" either. She sighed in defeat. "M'kay. You got me. I did say 'Glory.' But that's just, like, totally wild speculation, since he's been crushing on her forever. I have no way of knowing for sure."'

Katherine leaned into Amy's personal space with an intense stare. "Aims, don't lie to me! We ARE BFFs, right? We're closer than even close sisters, aren't we? I think you know more than you're letting on. I want you to tell me the truth!"

Amy withered under Katherine's stare. She turned her head in defeat. "M'kay. It's true. I do know more. I was talking to him about her a while back, and it kind of slipped out that they're involved."

Katherine stood up and slapped a fist on her open hand. "I knew it! I knew it!" She started to pace around the sun deck with both fists clenched. "Dammit!" After some more pacing, she growled, "As if the competition isn't tough enough already!"

Amy sat all the way up in her chair. "What do you mean 'I knew it?' You haven't said anything like that to me at all. Not even as speculation."

Katherine sighed. "Okay, maybe it's more like 'I should have known.' To be honest, I knew about his feelings for her, but I just wasn't able to believe that he could actually get it on with a teacher. Not even him! That could be a serious scandal! She could lose her job, easy!"

"I know! That's why it has to be a secret. You can't tell anyone."

Katherine's fists were still clenched as she returned to her lounge chair and plopped her bare ass down on it with a heavy sigh. "My emotions are all jumbled up. For one thing, that IS a lot more competition. Between her looks and his crush and the teacher taboo, this is a major development. This isn't another Joy or Janice type situation, that's for sure! But then again, I AM his fuck-toy sister and one of his personal cocksuckers, and I'm not supposed to get jealous when he's with one of his other conquests."

Amy said, "That's easy to say..."

Katherine finished off, "But damn hard to do! DAMN! I'm totally burning with jealousy right now! I'll bet my skin is turning green. Aims, do I look green?"

Amy giggled. "No. Definitely not. You're still Kat-colored."

Katherine stared off into space. "Damn! I feel green with envy though, that's for sure! And I'm pissed that you knew and I didn't."

Amy said, "Don't feel bad. It's super way double duper secret. It wasn't like he told me and didn't tell you. To be honest, I kinda got him to disclose it unintentionally, in a sorta sneaky way. And I don't think our moms know either."

Katherine sighed again. "Well, that makes me feel a little better, anyway. What else about this do you know?"

Amy held her hands up defensively. "That's it! Really! Aside from his one slip where he confessed they were involved, he hasn't said a word about it. And it's not like it's a long-term thing; I'm sure it's something that only happened recently, since his sexual confidence has been surging."

Katherine growled, and then stared off into space.

After a long pause, Amy asked "What are you thinking?"

"I'm imagining the two of them together. Have you noticed he hasn't been around for lunch lately, like, at all? I had assumed that he'd been spending that time with this or that cheerleader. But I'll bet he's been spending most of his lunches with HER! And that's the other thing. I'm burning with jealousy right now, but I'm also burning with lust! And the two burns merge together and create a raging inferno!"

Amy asked, "How so?"

Katherine exclaimed passionately, "Because it just proves all over again what a TOTAL STUD he is! My GOD! Is no woman safe from his rampaging dick?! I think not! He even fucks his sexy teachers! Isn't that hot? I think that's hot! Can you just imagine, the very same classroom where he sits and listens to her lecture, just like all the other students, once they're gone she's naked and bobbing on his cock like her life depends on it!"

"You don't know that for sure."

"No, but come on. You totally know it's true! And doesn't that make you horny?"

"Well ... to be honest..." Amy broke into a big grin. "Yeah!"

"Big time! I say we do something about it!"

Amy seductively suggested, "I still have bumps that need checking, if you know what I mean."

"I do! Say no more!"

The two of them quickly rushed off to Katherine's room to have some sexy fun of their own. They picked up their clothes as they left, but they didn't bother putting them back on.


Chapter 2

Suzanne tried to hurry home with Alan after their afternoon fucking session, but thanks to rush-hour traffic they didn't arrive until about 7:30 p.m. It was a long ride back from their hotel, but that turned out to be a good thing as it gave both of them a chance to recover. Between the ride and the showers they took before leaving the hotel, their freshly-fucked looks had faded and they appeared almost normal. But inside they were bereft of energy.

They talked about nothing in particular for a while, since they were both emotionally and physically tired. But at one point, Suzanne broke the silence by saying, "Soooo ... Susan told me that she broke the news about Ron being gay to you and the girls."

He moaned unhappily. "Oh, man! Do you really have to bring that up?"

"Yes, I do. Life is complicated, and we have to deal with the bad as well as the good. I was going to bring it up earlier, but I didn't want to ruin the mood of our 'computer shopping.' But tell me, now that you've had some time to consider it, what do you think about it?"

"To be honest, I'm trying not to think about it at all. Actually, I'm surprised at how easily I've been able to put it out of my mind. Mom told us about it right before my practice date with Christine, and I thought that would make me distracted and moody for the rest of the evening. But it turns out I pretty much forgot about it. And I haven't thought about it much since. I feel kind of guilty, like I should be more worked up about it."

She asked, "Why do you think that is?"

"I dunno. It's hard to get worked up about anything involving Ron. In fact, I mostly think about how this must hurt Mom. That's the main angle that hits me in the gut."

She said, "That's too bad."

He turned Suzanne's way and asked, "Aunt Suzy, you're kind of all-knowing. Why do you think he did that? Mom is such a generous, kind-hearted person. He wasted twenty years of her life with a fake marriage! I can't forgive him for that!"

Suzanne replied thoughtfully, "That really was a rotten thing to do, but I still think he's basically a good man. I think he found himself in way over his head. He probably was forced into the marriage by his family. Remember, things were different back then, especially in small-town Nebraska. I know that he loved you and Angel growing up, just as much as any father loves his kids. But then something happened about seven years ago that changed things. I can't tell you what, but I have a good idea."

Alan replied, "I can guess that well enough. That's when he found his lover in Thailand, right? So his loyalties shifted."

Actually, that wasn't what Suzanne was thinking at all. She strongly suspected that Ron had pulled away from the rest of the Plummer family around the time Alan hit puberty because he started to feel some sexual attraction to his son, and was so horrified by that that he decided the best way to make sure he never let those feelings grow was to stay far away as much as possible. It was just a theory, but she had seen occasional looks of anguish from Ron towards Alan during his rare visits home that told her she was right. However, Suzanne felt she couldn't possibly share that with Alan or it would ruin what was left of his relationship with Ron. Besides, it was only a hunch, without solid proof.

So she smiled enigmatically and said, "That may or may not be. Who knows?"

"A-ha!" Alan jumped to conclusions and took that for proof, just as she had hoped he'd do. Then he asked, "By the way, last night, when the four of us were talking about all this, we speculated that having this news coming out now is no coincidence. You timed this very carefully, didn't you?"

"I did. I knew there was something very wrong about Susan's marriage nearly from the beginning. But I also knew that your mom was so religious that she wouldn't agree to a divorce for anything. She would have shouldered the blame herself, even though she was blameless, which would have left her generally miserable. Her delusion that she had a normal marriage allowed you and Angel to be raised in a loving, successful way. I made sure to step in and fill the gaps caused by Ron's absence. In fact, he and I even had kind of an unspoken agreement about that."

"Huh?! What do you mean?"

"When he got his first assignment to spend all year overseas, he basically came to me and pleaded with me to step up in my role as 'auntie' to both you and your sister. Of course I said yes. He felt very bad about leaving, but felt it was something he had to do. It's complicated. Don't judge him until you know all the facts. There are some things I can't tell you now but you'll learn eventually."

She continued, "Anyway, the other factor is that I've sensed for a long time that your mom is highly submissive. She's great when she's taking directions from someone else, but she'd fall apart if she were on her own. That's why I timed things as I did. Now she has you. YOU have to step up, big time. I know you're not keen on the word 'master, ' but whatever you call it, she belongs to you now. Like it or not, she's YOUR responsibility from here on out. You've got to grow up fast. This isn't just sexual fun and games anymore. You really ARE 'the man of the house' in many ways. You and me, we're the ones who have to provide the leadership for this bunch."

Alan slumped in his seat and stared out into traffic. "Whoa. That's a pretty heavy load to place on an eighteen-year-old."

"I know, but that's life. A lot of guys your age are married with kids already. Anyway, it's not exactly all suffering for you." She gave him a sexy leer, and then winked.

He grinned back at that.

"Besides, I'm hardly 'all-knowing' like you say, but I do know a lot, and I'll always be there to help you in one way or another. You can count on me."

"Thanks! That makes me feel better. A lot better."

Suzanne stopped speaking for a while so he could ponder all that.

But Alan wasn't in a pondering mood. After just a few minutes of silence, he resumed talking, but about far less important matters. It was all too much for him to take at the moment. He would need to sleep on it and think about it later.

Then Suzanne said, "You know, as long as we've got a sufficient time to talk like this, it would be nice if you could give me another general update of your sexual adventures. I can't be your secret guardian angel if I don't know what's going on."

He smiled, and said sincerely, "I'd like that. I've been looking forward to getting some feedback from you on some things."

"Such as?"

"Well, Brenda, for one. Given what happened today, does that mean our overall strategic plan with her is complete? Can we mark that down as a big win?"

"Yes, we can mark that down as a big win for everyone involved, including Brenda. She's never been so happy, I'm sure. But, that said, our plan with her is not complete. Like I've told you, we're playing a very long game with her. Consider today the end of one chapter and the start of another. Now that she's sucked your cock and clearly loved it, expect a lot more of that. Fuck her face! Fuck her tits! Spread her legs and fuck her wet and needy cunt! Bend her over and fuck your cock all the way up her sex-slave ass until you're balls-deep inside her and she's convulsing in orgasmic overload all around you like she should. In short, treat her like the sex pet she so clearly wants to be!"

He actually shivered all over from the jolt of pleasure that exciting prospect induced. "So ... wait. What about playing aloof and hard to get?"

"Oh, definitely keep doing that. But you don't have to be so diligent about it anymore. She's clearly past the point of no return and in love with serving your cock, so have fun with her! Still, be sparing with your praise, and deliberately ignore her from time to time. That's not to be mean; that's what she expects from you. Also, it's good to continue setting hard-to-achieve goals for her. For instance, I made clear to her today that she's not one of your official personal cocksuckers yet, just because she blew you once. That title and status means a great deal to her, more than you know. It shouldn't come easy, or she won't value it very much. Other things, like fucking, also should be held out as future rewards."

He sighed heavily. "Ugh! Why is it that fucking is always delayed? With you, with Mom, with Brenda ... I mean, sure, I totally love blowjobs, but more actual fucking would be great."

Suzanne grinned slyly. "I couldn't agree more! But don't worry; things are finally starting to change. You just got to fuck me, didn't you?"

He brightened. "Thank God for that!"

She reached out and patted him briefly. "There's going to be a LOT more of that from now on, especially with me. But with Brenda, it's not yet time. The main thing is to continue to act domineering with her. You have to continue to live up to her high expectations. She thinks you basically walk on water. Let's make sure she keeps thinking that, especially with your sex skills and stamina and so forth."

He sighed again. "Man, that sucks. You know, I'm not really a dominant, alpha-male type guy. It doesn't come easily or naturally for me to be all cocky and confident around her."

"I suppose so. But aren't the rewards more than worth it?"

"Oh, definitely! But what IS the end game here? For instance, will I ever be able to totally let my hair down with her?"

"Hmmm ... probably not. But over time you'll get to know her better and better, and she'll know you better and better, and you'll be able to be more yourself. But even so, you need to keep that dominant attitude going at all times. Think of it like being a boss to an employee. You could become a really close friend to that person, but as long as you're the boss, there are certain ways you need to behave, certain things you can and can't do, even when you're hanging out outside of work. That's pretty much the same with Brenda. Just like you could have a boss status for years or even decades, you need to maintain dominant status with her for ... well, I don't know how long exactly - the future is unwritten - but maybe years or even decades too!"

"Really!" He stared at Suzanne in wide wonder. "I find that hard to believe. In fact, I still find everything about Brenda hard to believe. I continue to feel that she's way, way out of my league. It's not like with you, where we have a special connection based on our years together, basically all of my life. I feel like we're kind of bamboozling her, and if she saw the real me she'd lose all interest."

"That's not true. You're exactly what she wants. You're her dream man. Yes, you've gotta exaggerate certain traits some, but doesn't everyone do that to some degree? Especially in the early phases of a relationship, it's natural to try to look your best."

"True. But she shouldn't even know me. She should be on a massive yacht off the coast of some Caribbean island, hanging out with the likes of Tom Hanks and Bill Gates and Richard Branson. She's a multi-millionaire! You told me not that long ago that people are always striving for more, for something just out of reach, and that's why I have to play hard-to-get with her. But she could do soooo much better than me. Aren't women attracted to money and power? It makes sense, because they want a man who can be a good provider for their children."

Suzanne mulled over her thoughts before she answered, "There's some truth to that. But a little bit of pop psychology knowledge is a dangerous thing. She's had power and money up the wazoo; she was born wealthy. Look at what happened with her and her soon to be ex-husband, for instance. That didn't make her happy. She's actually burned out on that and liable to run in the opposite direction. Straight into your arms, actually. Well, okay ... more like into your crotch, if we want to get literal about it." She grinned at that.

She continued, "Besides, there are things we women look for in the man we want to father our children. But then there's also just pure lust, the things we look for in the man we want to fuck us silly! It's complicated. Sometimes, a woman just wants a wild one-night stand. You offer her that kind of excitement, but not just for one night. With you, it can go on for years and years to come."

He asked, "But is that possible?! How can that kind of sexual intensity be maintained that long? Especially with my focus and energy being split among so many women. Besides, now that she's experienced her sexual awakening with me, what's going to stop her from going to look for a man who gives her exactly what she wants sexually, PLUS he owns a massive yacht, runs his own company, and took part in the Olympics? There have to be at least a few guys out there like that."

"Maybe so. To be honest, Sweetie, we're sailing into uncharted waters. I don't know what'll happen. I don't even have a specific end game in mind for Brenda, just a general direction. But you have some huge advantages. For instance, you see your other women as a negative for her, but I believe it's actually a very big positive. She's not JUST falling for you, or your cock; she's falling for a whole group lifestyle. Frankly, I don't think she can ever go back to just a one-woman, one-man relationship anymore, not after getting a taste of how we live. So that rules out all but a minuscule fraction of one percent of all possible men for her. We have a VERY unique thing here. Not even men with their own yachts and companies have an entire harem of women. A mistress or two, maybe, but that's very different."

He winced. "Please don't use the 'H' word."

"Whatever. You know what I mean. The main thing is that she's so very submissive that as long as you maintain your dominant stance, you hardly have to lift a finger to arouse her. She does it to herself by talking to Susan about your exploits, being forced to share you with others, thinking and dreaming about you when you're not around ... I could go on. My point is, she's going to be hot to trot, with a VERY wet pussy, before you even open your mouth. Then she'll open HER mouth and create a tight lip-lock around your erection, and start to suck! End of story. She's happy, you're happy, it's all good."

He shook his head in wonder. "Man, that's so friggin' weird. I hear what you're saying, but I still can't really believe it. I mean, Brenda? Sucking my dick? It shouldn't happen. And yet it is. I chalk it up to your scheming brilliance. That's the only thing that can explain it."

Suzanne was tickled pink at that compliment, but tried not to show it. "By the way, speaking of Brenda sucking your cock, how was she?"

Brenda

He recalled how she'd looked, kneeling naked below him next to the pool, and shuddered as a jolt of excitement coursed through him. He replied with renewed eagerness, "Oh man! Don't get me started, or I'm going to get all horny. Technically speaking, she wasn't that good. Way below average, actually, if you compare her to the likes of you or Glory. But she made up for that with so much damn enthusiasm! I actually saw tears leaking from her eyes, which I think was due to her struggle and determination. How could that not arouse me? It kind of reminds me of Mom a while back. Nowadays, Mom has cocksucking passion AND a lot of skill. She's getting better by the day, and it makes me wonder just how awesome she can still get. But in the beginning she didn't know what she was doing and it was all passion. Even that was pretty damn great in its own way."

Suzanne was slightly miffed by that answer, because it made her wonder, Hmmm, it sounds like Susan could be getting better than me! I can't let that happen. And if he's right about Brenda, and I'm sure he is, then she'll follow the same progression. In a few weeks, she'll have both the passion AND the skill. Also, I noticed again his praise for Glory. I've got to step up my game if I want to keep my reputation as the most talented cocksucker around. At least I have deep throating and some other special tricks going for me.

In a sense, I've kind of created a monster with Brenda. With her in the mix, there's bound to be lots more competition for Sweetie's limited time, energy, and cum. I doubt we'll be able to limit her to seeing him just a couple of times a week, as I'd promised Susan and even myself. But, all in all, I don't have any regrets. She's such a dish! I can tell she's succumbing to her lesbian desires. I'll probably end up having as much sex with her as he will. And that's not counting the great orgies we'll all enjoy together! Her submissiveness can be a bit much, but it feels like she belongs with us.

He thought back to how Brenda looked when she'd been sucking him off earlier. "Besides, it's not just what she's doing with her mouth and hands. The fact that she looks like she does is a massive plus! Knowing that I have a perfect-ten centerfold-worthy babe bobbing on my dick is a constant thrill, no matter what. And of course I can look at her naked body as much as I want, and even fondle it to my heart's desire. So basically, she already gets an A grade simply from showing up!" He laughed.

Alan and Suzanne continued to talk about Brenda for a while. Then he gave her an update on how things were going with some of the other women in his life. However, he left out some of his more complex situations, in particular his relationship with Heather. It wasn't that he was trying to keep a secret; he just didn't want to deal with that unpleasant subject quite yet.


Chapter 3

Eventually, the conversation wound down again. Suzanne used that as an opportunity to say, "I've noticed you've talked about nearly all your lovers, but there's one you've failed to mention: Heather."

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