Six Times A Day
Part 24: Hard to Handle

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

Harem Incest Sex Story: Part 24: Hard to Handle - 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 45: Wednesday, October 30

Chapter 1

Alan woke up Wednesday morning feeling weary but excited. He was weary because he hadn't been able to sleep as much as he needed; he was wiped out from so many great sexual experiences.

He was also excited, because he sensed that his mother had reached some kind of tipping point. Their path forward wasn't clear, but it was obvious that there was no going back. That was an absolutely huge development, because she was the linchpin to sexual permissiveness at home.

Unfortunately, when he came down for breakfast, Ron was there, reading a newspaper and eating scrambled eggs and fried tomatoes, with Susan cooking in the kitchen. It was all so painfully traditional that Alan didn't know whether to laugh or cry.

Susan had resumed wearing her old clothes, including her usual apron. She showed only the slightest hint of cleavage. She glanced at him with a friendly smile and "good morning" greeting, but that was it.

When Alan went to his room to get his backpack and school books, Susan came in and closed the door. Looking nervous and guilty, she said, "Tiger, what we did yesterday was ... not a bad thing. I'm happy to help you with your medical problem, as long as you remember that what I said and did was just to help inspire you. But you need to forget about those wild things I said in the heat of the moment, okay?"

He nodded, although there was no way he would ever forget.

She said, "I've been thinking about your father. True, things haven't been good between him and me, and our sex life died long ago, if it ever really existed in the first place, but can I really blame him for that? The way I used to be - a cold fish in bed, literally frightened and ashamed about sex - that's at least partly my fault, due to my prudish hang-ups."

She continued, leaning against Alan's door as she talked, as if to hold it shut. "In any case, what we're doing behind his back ... it isn't right. I believe he's basically a good person."

He wanted to speak out about the problems between her and Ron, but knew that it wasn't his place. He figured the situation would probably resolve itself soon, since he was sure that, due to all the dramatic sexual developments in the house, Susan's marriage was doomed regardless. He didn't want to look like he was trying to usurp Ron's place as Susan's sex partner, even though that's what he actually wanted to do. Furthermore, he thought the best thing to do when she was going through one of her now-common mood swings was to just be agreeable until it blew over. So he responded simply by nodding with understanding.

She continued, "Even just talking to you right now makes me feel sinful and guilty. Now that your abnormality check is done for the week, can we just go back to being a normal family until he leaves? That's only two more days. Can you take care of things yourself for two days? Maybe with whoever your mystery assistants are at school?"

"Sure, Mom. That sounds completely reasonable. But you forgot to mention Aunt Suzy. She can be a big help."

"No, I didn't. She's kind of in my doghouse right now. She's been pushing me too hard, making me do crazy things. I wouldn't have gone so far lately if it hadn't been ... Well, let's just say that I think it'll be good if she cools it for a couple of days too. She means well - I know she does - but when she gets carried away, her advice isn't always that good."

Dang! Major cock block! What a drag. But he said, "Okay. Whatever you say. Sorry if you feel like I've been pushing you into things you don't want to do. And I know Aunt Suzy means well, so I hope you're not too upset with her."

He seemed to be done, but then he added, "That said ... It just occurred to me that if you can't help, and Aunt Suzy can't help, then what's going to happen? You don't want me to commit the sin of Onan, do you? I thought we were past that."

"Oh dear me. No! Not that! Anything but that!" She frowned with worry, then asked, "What about your big-titted cheerleaders at school? Can't they pick up the slack?"

He flashed back to what had happened with Heather the day before. As great as it was, he highly doubted it would happen with her again. But that still left him getting help from Glory and Kim. "Mom, I'm getting help from at least one female at school, but I can't say who or how many. Anyway, that's at school only; it doesn't help at all when I'm home."

She asked, "What about Brenda? You'll be seeing her tonight, you know. And Suzanne says you're all set to wow her."

"Maybe so, but that's just to talk. She also says it will take WEEEKS to seduce Brenda. So that doesn't help at the moment."

Susan's frown deepened. "Oh. Oh dear. What about your other mystery helper, then? For instance, the four mysterious checkmarks on your orgasm chart from Saturday?"

He spoke carefully, since he didn't want to reveal the help Katherine was providing. "I can't talk about that at all. Sorry." Then he lied, "But that doesn't help at home anyway." Then, hoping to get Katherine's participation out in the open, he suggested, "What about Sis? She's eager to help me, and she's been great with the visual stimulation."

Susan was adamant, folding her arms under her massive rack. "Definitely not! She's not ready."

"How 'bout if you and Aunt Suzy just help with handjobs for now? That's not so bad."

She fretted, looking nervously all around the room. "Well, I don't know. I'll think about it. Okay?"

"Thanks, Mom! You're the best. Nut now I've really gotta run or I'll be late for school."

As he left, Susan gave him a non-sexual kiss and hug. It was like the old days before his treatment began, when she'd been reluctant to even hug.

As soon as Alan was alone, he thought, That sucks, big time. But on the bright side, at least Mom isn't mad at me and she hasn't fallen back into full-on prudish mode. She did say "What we did yesterday was ... not a bad thing." That's really major! All I have to do is wait two days for Ron to leave and hopefully things will change around here again. Maybe sooner. Besides, getting it on with Aunt Suzy, Glory, and a sexy cheerleader or two at school is like a billion times better than my best-case scenario just a couple of weeks ago! I actually got to fuck HEATHER yesterday! Pinch me; I'm dreaming, 'cos I still don't believe it.

Then there's Sis, who's turning out to be a real wild card. Who knows what could happen with her, and when? Maybe we can sneak away for a couple of hours, like we did over the weekend. Hey, the next couple of days are actually looking pretty good! In fact, when it comes to the long term, "the future's so bright, I gotta wear shades," as the song goes. Things are progressing nicely on a lot of fronts, including maybe with Brenda. Heck, the fact that there even ARE fronts is awesome! Besides, now that I think about it, Sis and I have a session at Kim's house tomorrow afternoon, so that's another awesome thing to look forward to. Cheerleader orgy! Woo-hoo!


The new bright spot of Alan's school day was his private time with Glory.

She had resigned herself to the fact that their sexual relationship was for real, and it was pointless for her to continue trying to deny her feelings for him or think that she'd bring it to an end, at least any time soon. She couldn't wait.

Unfortunately for Alan, he wasn't up for more sexy fun. In mind, yes, but not in body; his penis was still recovering from his "sex binge" of the previous day.

Glory's hands were on his crotch almost the instant the last of the other students had gone, but his dick had been so overworked that even getting hard was painful for him. His lack of response led her to wonder about the explanation.

Glory fondling Alan's crotch, attempting to get him hard

She pulled down the elastic waistband of his outerwear shorts and placed her hand on the bulge in his underwear. What she found was flaccid. "Alan, is there something wrong? We've been together three times and you're already tired of me?"

"No way, Glory," he replied. "I've been whistling 'The Battle Hymn of the Republic' all day long." That was true, since he was referring to his 'Glory, Glory, Hallelujah' version. "But my dick hurts. It really does. Why don't we practice kissing?"

So Glory had to content herself with kissing and groping. The gossipy teacher wondered to herself what, or more likely who, had gotten his cock so worn out, but she resisted the urge to pry. She was afraid of the answer.

After a few minutes of tender cuddling, she came up with an idea. "You know, we talked about varying things up. Not just meeting at lunch, but after school sometimes too, as well as not meeting at all on some days. What if we try to meet after school today?"

He thought, Man, this is like a dream come true, that the woman of my fantasies is asking me that. But I'm pretty darn wiped out. Plus, maybe there'll be some kind of sexy fun when I get home. Could I handle Glory AND whatever sweet delights await me there?

He admitted, "I'm not sure. If I can't get it up for you now, will that change in less than two hours? Maybe my body is telling me to take the whole day off."

"But you can't. Aren't you more or less required to cum a lot every day, regardless?" She had serious doubts about the validity of his orgasmic treatment, but she was willing to use it to her advantage in the moment.

"That's true."

She thought back to the great time they'd had the day before when she'd dressed up as a police woman. "Hey, I have an idea. What if I dress up in something special and we have another role-play? Wouldn't that inspire you?"

He replied sincerely, "To be honest, merely thinking about you inspires me plenty. It's just that I'm not sure if it's smart for me to be inspired today. Maybe when my body tells me to take it easy, I should listen."

"Pshaw. You've gotta push yourself or you'll never run a marathon or accomplish anything major. If you're not out-and-out hurting, I'm sure it'll be fine. Tell you what. I'll sweeten the pot even more. Remember how I gave you a spanking on Friday?"

"How could I forget?"

"Turnabout is fair play. Maybe it's time for you to spank ME! You can be the teacher, and I'll be the naughty student who needs to be punished."

"Are you kidding me?!"

"I'm serious." She was warming to the idea the more she thought about it.

"I'm so there! Even if I have to crawl over a field of broken glass. Man! Glory, you're the best! I don't deserve you!"

She chuckled. "That's true. Still, it seems you're stuck with me." She abruptly pulled herself from his embrace. "Now, go eat lunch with your friends. You don't want to make a habit of skipping lunch to be with me."

He left a short time later when she practically pushed him out the door. She was in a hurry because her mind was racing with her role-play idea, and she wanted to do it up right. She figured there was just enough time for her to race home, grab some clothes, and race back before the start of fifth period, so that's exactly what she did.


Chapter 2

Alan had a hard time concentrating through his fifth- and sixth-period classes. All he could think about was the promised after-school role-play and spanking with Glory. He knew his worries about not being able to get erect were unfounded, because he got plenty erect just thinking about it. Playing tennis kept him busy and flaccid for most of sixth period, but as soon as tennis was over, it was like he had an iron bar in his shorts.

It was almost torturous to make his way slowly to Glory's classroom after the final bell ring. He wanted to run, but forced himself to walk. The upside was that by the time he got there, all of her students were gone. In fact, she was just as eager as he was; she'd even managed to change into the clothes she'd snatched from home by the time he knocked on her door.

Once she confirmed it was him and him alone, she let him in.

It was a very good thing that the hallway was empty, because he just stood and stared at the sexy vision standing before him. My GOD! Why does things like this keep happening to me?! It's like everything is sexually supercharged all of a sudden, and I don't know why. But, dang! Who needs a why when she looks this good?!

Glory carefully and quickly walked around him, closed the door, made sure it was locked, and then resumed her position in front of him. She wasn't striking a particularly sexy pose, but she didn't have to, because her outfit was jaw-dropping enough. Thanks to the clothes she'd picked up from home, she was playing the role of the naughty schoolgirl to the hilt.

Glory

She was wearing a red-and-white striped top that covered her shoulders and upper arms, and not much else. Her boobs were dramatically exposed, with just her nipples just barely covered. The top was tied just under her rack, leaving all of her tummy bare. It was clear she wasn't wearing a bra.

She wore short jeans shorts slung low on her hips. As if that wasn't revealing enough, she'd left them unzipped, exposing the top of her bush. She held some textbooks in one hand to complete the student look. She also wore high heels, which, although they didn't really fit the schoolgirl motif, definitely made her legs and ass look even more enticing than usual.

She said, "So, Mr. P., I hear you wanted to see me about something?"

Since Alan had been thinking of little else the past two hours except their role-play, he already had his teacher persona to slip into. He barked, "That's Mr. Plummer to you, Glory. Look at you! You know you can't come to school dressed like that!"

Glory struck a deferential pose, clutching the textbooks to her midriff and dropping her head. "I'm sorry, Mr. Plummer. It's just that..."

"What? You know I'll have to punish you. What were you thinking?! I can even see some of your, well, your hair ... down below! It's outrageous!"

Glory acted shy and embarrassed. "To be honest, sir, I just pulled my shorts down a couple of inches. You're the only one who gets to see me like this."

"And why would you do that? Glory, you've been my most difficult student, by far. Always getting into trouble. Well, it stops today. If you're going to act like a willful child, then I'm going to treat you like one! You leave me no choice but to give you a spanking!"

She nodded, while still obediently looking to the floor. "Yes, sir. Mr. Plummer, sir."

He waved a hand imperiously and impatiently. "You know the routine. Take off your clothes and bend over my desk."

"Take off my clothes, sir? All of them?!" She put her textbooks down and started fiddling at the knot of fabric just under her breasts.

"Certainly. I'm not going to let you get away with blunting the force of the spanking with your thick jeans shorts. I'd let you keep your panties on, but you're obviously not wearing any. That's another rule violation, by the way. I'll have to give you another ten smacks for that!"

Glory had already been highly aroused in anticipation, but she was getting even wetter and more aroused in response to Alan's confidence and authority. He really seemed like a take-charge teacher. She bent over outrageously and pulled her jeans shorts down her legs. However, she just had to ask, "Fair enough, but why do I have to take my top off too?"

"For starters, you're hardly wearing a top to begin with. I'm going to have to confiscate your clothes since they clearly fail to meet the minimum school requirements. Secondly, who says I'm only going to spank your ass? Since you're showing an outrageous amount of cleavage, perhaps you need to be spanked there as well."

She didn't know if he was serious about that. She'd never even heard of such a thing. But she knew that, even though the role-play was feigned, the spanking she was about to receive would feel very real. She thrilled to think he might spank her breasts too - provided he did it in a sexy way and not a truly painful one.

He stood watching in impassive silence when she took her clothes all the way off (except for her high heels, of course). However, she could tell his poker face was an act by the way his shorts were tenting outrageously. That made her smile. I don't know what's going to happen with this spanking, and I can't wait to find out! But I DO know that he's not about to get out of here until I have my lips around his fat cock and I suck him to a cummy explosion! Since we can't fuck, I'm going to turn cocksucking into something that will absolutely melt our brains!

Indeed, Alan was so excited that it was a marvel he wasn't romping around the room and bouncing off the walls. I don't know which is better: Glory in her naughty schoolgirl outfit, or when she's buck naked. I'm a total winner either way! DANG! There's so much misery and trouble in the world. But at a time like this, I'm flying far from the Earth, basking in pure joy! It was awesome enough to do something like this with a total hottie like Heather, but this is my history teacher, for crying out loud! I wish I could tell somebody! But who would believe it?! Hell, it's happening to me right now, and even I can barely believe it!

Now that she was naked, Glory stood straight like a soldier, with her hands behind her back and her legs spread straight and wide. "Mr. Plummer, sir? Where do you want me?"

He pointed to Glory's desk in front of the classroom. "Bend over my desk, of course." But then he got an even more wicked idea. "No, wait. Clear the desk off. Sweep the papers to the floor if need be. Then crawl onto the desk on all fours."

Glory almost dropped her role, because she considered that too outrageous. "Are you serious?!" Then she thought, Hell, why not?! It's big enough, and it can easily support my weight. I'll never, ever see my desk in the same way, but so what? God damn! This is why Alan thrills me in a way Garth could never even imagine. I love it!

He was starting to have second thoughts. In truth, he wasn't nearly as confident as he seemed.

But before he could take back what he'd said, her expression totally changed. She flashed him a naughty smile and said, "Yes, sir!" Then she crawled up on her desk. She deliberately positioned herself so he'd be able to walk up behind her and easily reach her thrust-out ass.

He walked behind her and brazenly caressed her bare ass cheeks with both hands. Then he quickly yanked his shorts all the way off. It was a great relief to have his raging erection fully freed. He went right back to fondling her ass.

He felt so giddy and triumphant that he was almost dizzy. He thought, This is where my recent experience with my other sexy ladies pays off. The old me could never have handled this, because my brain would have exploded several times over by now. Everything is too fucking sexy to take! I doubt there's ANY other student in this school who could cope with spanking our total fox of a teacher while she's naked and on all fours on top of her own friggin' desk! But can handle it, thanks to all the super sexy stuff I've done back home. Fuckin' A!

He took some moments to close his eyes and breathe deeply. Then he tried to get back into the teacher mindset. As he continued to blatantly run his hands all over Glory's ass, he said, "I've heard rumors about you. Very nasty rumors, that you're a total slut. They say you'll put out for just anybody. Is that true?"

"Mr. Plummer, sir! I must protest! That's completely untrue! I, I ... If you must know ... I have a crush on one of my teachers, and I'm not interested in anyone else! That's the only reason I dress like I do!"

She didn't need to say that he was the teacher, because they both knew that's what she meant.

She thought, What a kick! What a total rush! This is what I call truly living! I'm on the verge of cumming from the hair on my head to the tips of my toes, and he hasn't even started the spanking yet! It's a good thing we're not trying this at lunch, because the chairs are going to be floating in a lake of my pungent cum before we're through!

She panted, "Sir! Do what you have to do! I've been bad and you need to spank it right out of me!"

"Indeed. Brace yourself! Here it comes!" He was far too excited to think about establishing some kind of verbal procedure. Instead, he held her in place with a hand on one ass cheek, and then smacked her hard on the other.

She cried out. She was surprised how hard the smack was. She'd figured this was going to be a sexy spanking, not a "real" one in any sense. But the smack was as hard as she'd expected a truly disciplinary spanking to be. She complained, "OUCH! DAMN!"

He said, "Sorry, Glory. Spare the rod and spoil the slut. I can't go easy on you, or you'll never learn. It's for your own good." As he spoke, he caressed both her ass cheeks like he'd been doing. But, for the first time, his fingers explored their way into her ass crack, and below, along her perineum (taint) to her soaked pussy lips.

When he reached the latter he said, "I'm concerned that you'll find this arousing instead of punitive. That's why I can't go easy on you. We both know you have a crush on me, and you've had one for a long time. That's why I have to remain strictly professional." Even as he said that, he pressed a finger against her clit, causing her to moan with erotic need.

Then he abruptly pulled his hands away, raised one up high, and swung it down on her other ass cheek.

Again she cried out. Then she complained, "OUCH! Mr. Plummer, PLEASE!" She loved that she was calling him "Mr. Plummer." Actually, she loved absolutely everything about this, especially the complete role reversal. She'd never been sexually spanked before in her life, and she didn't consider herself the submissive type. She highly doubted this was something she'd want to do often, because it did hurt a lot, but it was great as an occasional surprise.

"Please what?" His hands were right back fondling her, freely running all over her ass and pussy mound. As he ran the tip of his index finger up and down her wet pussy lips he said, "I'm concerned you're not taking this seriously. I told you this is to punish you, not to arouse. That's why I'm checking you down here."

She thrust her ass back at him, hoping to get his finger to slip inside her. "Mr. Plummer! If you keep checking, I'm going to lose it! Don't check so much!" When she said "lose it," she was talking about cumming. She'd been on the verge of cumming before the spanking even began, and now that it was in process she was hanging on for dear life.

Alan could sense how worked up she was, and he greatly desired to give her a big "O." So he sped up his efforts. He smacked her ass several more times, in relatively quick succession. But it was only quick in comparison to the first two, because he spent a lot of time between smacks "checking" her arousal, most especially by stimulating her slit and clit every way he knew how.

After the sixth smack, she lost control. She'd been humping back at his hand without a shred of dignity or restraint, when out of the blue she let out a piercing wail. Her entire body trembled as her much-needed orgasm slammed into her. She had to brace herself to some extent, because there wasn't much desk surface on either side of her, and she was afraid of falling to the floor.

He loved the pleasure he was giving her. But he was also eager to cum himself, or at least get close to it. Although his shorts were pulled off, his erection wasn't getting any "action" at all.

Glory remained on all fours on top of her desk, mostly because she didn't have much room to do anything else.

As her gorgeous, fit body continued to heave and pant while orgasmic aftershocks coursed through her over and over again, Alan crawled up on the desk behind her. He knew it was a bit dodgy, but the desk looked to be a solidly built one and he though it could support them both. He didn't have much room, but he wanted to get his boner involved. He removed his shirt and even his socks, because he got off on the idea of being completely naked on top of his teacher's desk.

He resumed fondling her ass and pussy, to her great delight. But then she stiffened with alarm when she felt him guide his cock up to her inner thighs. She spoke in a highly alarmed voice. "Time out! What do you think you're doing, young man?!"

He said sheepishly, "Just ... I thought this looked like fun..."

"Of course it does, but don't think for a SECOND that I'm about to let you fuck me! Get that thought out of your head! I told you that's not possible until we get the nature of our relationship established, if we can do that at all. I've been having the time of my life. Don't ruin it by trying to push too far!"

The idea of fucking her was definitely on his mind, but she objected so strongly and passionately that he lowered his expectations. "Glory, trust me. I definitely am NOT going to do that! I just kind of want to rub it against you in that area. You know me; I'm a nice guy. I don't want to ruin our new relationship before it even gets very far. Please believe me! I will NOT do that to you today. I promise!"

She grumbled, "Maybe those are your intentions, but accidents do happen. It's too dangerous!"

"What if I do this?" Holding his erection up, he rested it up against her ass crack, so the tip was pointing above her. It was well away from her pussy.

"Well ... I don't know. Maybe. I suppose we can try it for a minute."

YES! Sweetness! He tried to get back into teacher mode. "Okay, Glory, let's resume your spanking. I'm keeping my dick where it is to, uh..." - he scrambled to come up with even a half-baked excuse - "um, to, uh ... to test your resolve. Your, uh, willpower. Okay? Here we go. Brace yourself!"

Glory

He resumed his earlier pattern of occasionally smacking her while spending more time fondling her ass and pussy. The only problem was, with his cock nestled in the groove of her ass crack, he was in danger of accidentally smacking himself in a very, very painful way. He tried to avoid that by smacking the outer sides of her ass cheeks, down by the tops of her thighs. That helped some, but still, his boner bounced around after each smack.

After a few more smacks, he admitted defeat and repositioned with his penis below her pussy, as if he was about to dry hump her. That was much better in case of an off-target smack, but it greatly increased the danger of accidentally sliding his cock into her pussy, just as she feared.

Glory realized the likelihood of them fucking, accidentally or not, was increasing by the moment, and she wasn't ready for that. She was alarmed because she found herself ardently wishing that he'd just slip it into her already and give her a solid pounding.

To prevent that from happening before she lost all control, she carefully repositioned on the desk. It wasn't easy, but she managed to turn herself all the way around. Then, still on her knees but with her face in his crotch, she took his cock in hand and fed it into her mouth. She started to suck.

That effectively ended the spanking, since he could no longer reach her ass. It effectively ended the role-play as well, since she was unable to talk. However, neither of them minded one bit. Alan had been worked up to a fever pitch, so he was grateful for the sudden direct attention to his cock.

The only downside was that he was so very aroused that he couldn't hold out once she started sucking. In fact, he lasted only a few minutes, and even that was a near epic struggle. With a loud, wordless cry, he erupted into her hot, greedy mouth.

She sucked him through his orgasm, continuing until he went flaccid. She didn't have another orgasm of her own, but she didn't really crave one since she'd just had an enormous one a few minutes earlier. She managed to savor a lot of his cum on her tongue, but nearly all of it went down her throat before long, leaving her face clean.

Once it was over, the two of them crawled down from the desk and rested against it, side by side. They kissed and cuddled a little, but they were too exhausted to do any more than that.

After they were fully recovered, Glory gave him a mini-lecture about the danger of getting that close to fucking. She reiterated her intention not to fuck as long as they were just "sex friends."

He promised that he would be more careful in the future.

They were both completely sexually satiated and tired, so Alan headed home not long afterwards, once he helped her clean up and cover the smell of sex in her classroom.


Chapter 3

Alan went home hopeful that he could take it easy for a while. After what had happened with Glory, he figured he'd take a nap before he even contemplated any more sexual activity.

 
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