6 Times a Day

Chapter 1105 Alan’s small Harem!

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William Osborne, Jesse Boyer

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Alan had a difficult time in his fifth-period calculus class. His penis kept getting hard for no reason, and there was nothing he could do about it. His teacher, Mrs. Metzger, was old and unattractive, but that didn’t matter, since he wasn’t paying much attention to her anyway. Images kept popping up in his mind such as a naked Christine draped over him “like Saran wrap.” He envisioned Christine, his mother, and Suzanne thrusting their racks into each other, Heather being sexually molested by the entire cheerleading squad, saw himself fucking a deliriously happy Glory in front of a bound, naked, and angry Heather, and much more. Mostly, he remembered the sight of Heather bent over Glory’s desk.

Needless to say, these thoughts were not helping him get rid of his hard-on.

Worse, Janice was in his class, and he really wanted to get a message to her, but she sat on the other side of the room. Passing a note containing any useful instructions would be far too dangerous. When class was over he tried to reach her, but she was gone in a flash and he had no chance.

He stood outside the class trying to see which way Janice had gone when Christine rushed up, all out of breath. “Alan! It’s so good to see you! Do you mind if I tag along?”

They were in a crowded hall, and Alan could see that Christine was playing to an audience, trying out her new lovestruck “cover story.” Alan tried to play along, though he was slightly miffed that her presence denied him another chance to duck down a hallway and get some desperately needed relief for his blue balls.

Her presence led to a surge in his Christine fantasies. As she talked, he found himself thinking about how her lips would look and feel as they opened up to worshipfully take in his throbbing penis.

Then, as if reading his mind, completely out the blue, she said in a harsh voice, “Alan, having so many lovers at once is wrong. It’s immoral, and I won’t stand for it.”

He was taken aback. He asked, “Where did that come from?”

Her face seemed to go from anger to worry in a heartbeat. She looked around and said, “Never mind. Maybe later we can talk abo- No. Just forget it.” She looked sad.

They walked together down the hallway in silence for a minute or two after that.

Alan was grateful he’d managed to avoid that discussion, and tried not to say anything that might get her started on it again. To his surprise, she didn’t try to pass him any serious information, though she did leave with a pointed, “I’ll see you after school.”

Alan also looked for, but failed to see, any of the cheerleaders or Simone. He especially hoped to find Amy or Katherine to help warn them, but they weren’t around.

He did run into Sean, however, and was glad about that. He needed to talk to him about a few things. Some of them, like the latest on his football player troubles, could be discussed in front of Christine. But others, like the need for Sean to get home quickly after school in time for Alan’s surprise for him, definitely could not. And in any case, with all the searching for the others there was no time to discuss anything in private. So he just told Sean to make sure to meet him after school.

Sean naturally agreed. Sean also looked curiously at the way Christine was staring at Alan with lovestruck eyes. She seemed to be having a ball playing up her pretend wanna-be girlfriend role.

Alan thought, Sean must be thinking: “Lucky bastard! As if he doesn’t have enough women, now even Christine is falling for him in a big way.” I should probably tell him soon that this, for once, is just pretend. At least, I THINK it is. Right?

And in any case, I’ve already made my decision not to get physically involved with Christine, and I plan to stick with it. If I end up sleeping with her and dragging her into my freaky sex-obsessed harem world, then the “Bad Alan” has won. She’s just too good and pure for that, and it’s not fair to my other loved ones to divide my attention up still further. So this pretend girlfriend thing is as far as it goes. I’m drawing a line in the sand on that, and nothing is going to get me to change my mind.

Alan didn’t say much to Sean or Christine before they had to part for their classes. The truth was, he felt sluggish and out of sorts. The football player woes and his blue balls were getting him down.

His penis was so hard by this point that he thought it was a bit of a wonder that he could walk around without crouching over in the most obvious way. He had to take a couple of minutes and focus on an image of a nude Henry Kissinger eating greasy fried chicken before his penis softened up a bit.

Given his relentlessly horny mood, the last thing he wanted to do was play tennis, but that’s what he had to do. As he sat in the locker room changing into his tennis clothes, he brainstormed for any excuse to get out of class. Then it hit him: a solution so obvious that he had to smack himself on the forehead. He realized that he still had the hall pass that Glory wrote for him in his pocket. It was the kind of a pass that was only good for a short break, like a quick trip to the nurse or the principal’s office, so he couldn’t get out of tennis altogether.

But he walked up to his tennis coach before class began and said, “Excuse me, but I have this pass, so I won’t be able to make the whole class. I’m supposed to help out with moving some stuff right before the end of school.”

The teacher nodded, uninterested. Alan still had his academic-star reputation, so no hanky-panky was suspected.

But hanky-panky was exactly what was on Alan’s mind. He hit a tennis ball back and forth, but his mind was elsewhere. He wondered, How early can I dodge out of class and make it over to the cheerleader practice in the theater room without making waves with my teacher?

In the end, he lasted about thirty minutes before hanging up his racquet. It was all he could do not to run to see the cheerleaders, but again he didn’t want to draw attention to himself. He knew he wouldn’t be right until he ejaculated; he’d just been too stimulated for too long to think straight.

He’d passed his key to the theater room to Katherine well before lunch, because he’d had no plans on using it and he needed to give it to Amy or Katherine every day before cheerleader practice so their practice could take place. Normally this wasn’t a problem, but today it meant that he had to knock on the door. Luckily, he had worked out a special knock with everyone on the “list” for occasions such as this.

Katherine opened the door, which gave Alan a small surprise. Just before opening the door she’d thrown on her cheerleader uniform and the others had retreated behind the curtain on the theater stage to be on the safe side, in case it turned out to be someone else. But the smell of sex was heavy in the air, so Alan knew the cheerleader orgy that he’d ordered must be in full swing.

Katherine had the door opened just a crack, but she pulled it wide and hustled him in. Once it was safely closed, she exclaimed, “Brother! What are you doing here?”

“I was going to ask you the same question,” he replied.

He looked up and saw the theater curtain part and then open wide. To his delight, the other cheerleaders were all in various states of undress. Heather was in the middle of it all. Her hands were tied behind her back with lots of rope, and she was gagged as well (but not blindfolded). Since they were in the middle of the stage, it looked like the opening act to the most debauched play ever conceived.

Aaaah, now that’s more like it! he thought with relief. This is normality for me, and something like playing tennis is what’s weird!

Kim came bounding down the stage stairs and past all the empty chairs to meet him. “Alan! Thank God! You scared the shit out of us!” She wore just her cheerleader top. She kept it on as she came to him, perhaps feeling self-conscious about the relatively small size of her breasts.

“Sorry for the surprise,” he said, “but I realized I had a hall pass and came to check on things.”

Kim caught up to him and got up on her tiptoes to kiss him fully on the lips. She wrapped her half-naked body around his and began grinding and pressing into him. His erection was at full mast by the time he got to the door, and she made sure to grind against his bulge in particular.

The kiss looked like it would soon turn into a full-on body grope, but before that could happen Alan turned to his sister, still standing there. “Sis, sorry to say this, but you should probably go, unless you want to see your brother do all kinds of unbrotherly stuff.” He belatedly realized he shouldn’t have put it that way, because her eyes lit up as if to say, “That sounds fine to me!”

But after that minor slip-up, Katherine kept her cool and managed a pout. “Damn. I miss out on everything. I guess I’ll go outside and… I dunno… get lost for a while, I guess.”

Kim, meanwhile, was already entranced by Alan’s rampant erection and grabbing at it with both hands through his pants. Despite the pants being there, she could nearly wrap her hands around it, and that’s what she was doing. She seemed to pay no mind to the fact that Alan’s sister was standing right next to her.

However, Alan suggested, “Sis, why don’t you just take off for home? No one is going to be expecting that. That’s a lot safer than just hanging around.” He didn’t want to speak directly of the football player troubles with the other cheerleaders in earshot, but he assumed she would understand what he was talking about, and she did. .

Suddenly a great big frustrated moan came from Heather’s direction. She’d been quiet and still, but now she was frantically trying to break free from her bonds.

Katherine continued to look Alan in the eye and pretended not to hear the sound of a zipper unzipping. She giggled. “I don’t think Heather likes the idea of me going home early. You see, Heather basically runs the cheerleader squad with no supervision. But if one of us were to get caught doing something illegal like skipping school, her ass would be grass.”

Alan briefly glanced down to see Kim’s hands wrapped around his bared erection. He tried to act as if that wasn’t happening, since his sister was still standing right there (and trying very hard to only look him in the face).

Then he glanced over at Heather. He marveled at the way the head cheerleader looked: bound, gagged, writhing, and moaning, all the while surrounded by a bevy of naked beauties. He could feel his penis grow even harder in Kim’s hands as he stared. “Well, we wouldn’t want to do anything that Heather might not approve of,” he said with great sarcasm.

Katherine winked. “Oh. Right. Then I just WON’T go home right now.” She winked again, and said in a quieter voice, “Don’t worry, I’ll be careful. Believe it or not, one of Christine’s friends gave me a special pager not an hour ago. It’s got some kind of GPS tracking thing or something. I don’t understand it all, but it’s supposed to be a safety thing. So I’ll be fine. Don’t have too much fun without me, okay?”

She almost put her hand over her mouth in embarrassment after saying this, but decided to brave it out instead and just keep talking. “Oh, and Amy’s got the key now.”

Alan had very carefully turned his whole body away from his sister and had to look over his shoulder to maintain eye contact with her, because Kim simply couldn’t wait. Kim’s only nod towards any self-control was to hold herself to merely jacking him off with both hands until Katherine left instead of fully blowing him already. After all, she’d seen Alan and Katherine have sex lots of times so it was hard to pretend to be clueless about the incest when there was such a delicious erection so throbbing, hot, and stiff so close at hand. 𝘳𝑎.𝗇t

Since Katherine was already dressed, she picked up her backpack and put her hand on the door. She looked at Kim out of the corner of her eye and said in her best imitation of Sergeant Schultz on Hogan’s Heroes, “I know nussink! Nussink!” Then she giggled and left.

The other girls waited for the door to close behind her. As soon as it did, Janice shouted, “Paaar-tyyyy!” It was as if everyone had been holding their breath until Katherine left, and now they could exhale.

Suddenly, all of them seemed to be talking to Alan at once. Even Heather moaned loudly into her gag.

Kim attempted to drop to her knees – for someone who claimed to love women more than men, she had a remarkably strong passion for cocksucking.

But Alan held her up and began walking to the stage.

Kim did what she could to satisfy her lust, continuing to stroke his hardness with both hands while he walked to where the others remained clustered around Heather.

Janice, Joy, Kim, and Amy were busy talking to him, welcoming him, and propositioning him, but he couldn’t make any sense of so many voices at once.

Heather moaned loudly, but her gag muffled whatever she was trying to say. What had happened between her, Simone, and Alan before school was on her mind and making her extremely aroused.

Any pieces of clothing remaining on any of the girls was quickly coming off.

Amy stood up and gave him a long French kiss, but that hardly quelled the commotion at all.

So, with Amy draped around him and Kim’s hands still apparently trying to surgically attach themselves to his penis, he raised up a hand. A sudden silence fell.

“That’s better,” he said, satisfied. Mere weeks ago, he would have freaked out at such a situation, worrying how he could possibly please so many girls at once. But now he felt at ease and in his element. He said almost as an aside, “Kim, blow me. You’re good at that.”

Kim got to it right away. She was very good at it indeed, and in no time she had him on the verge of cumming and squeezing his PC muscle. In his current state, it didn’t take much.

But he continued to act nonchalant, even with Kim bobbing up and down over his erection. He pointed to Janice, who was pulling her cheerleader top off. “Janice, let’s hear the report. How goes it with Her Royal Bitchiness? Did she spill her secrets?”

“Unfortunately not. We’ve been having a hard time with her, as you might expect. She isn’t naturally submissive to us like she is with you. In fact, when we first- … Well, let me back up. In the locker room, it was like the calm before the storm, because everyone knew what was going to happen but no one could talk with other girls milling around. But as soon as we all arrived here, Heather tried to take charge. She said that she was the head cheerleader and she made the rules, blah, blah, blah. It actually ended up in a kind of a cat fight. All of us had to gang tackle her, pretty much. She put up quite a fight, too. Scratched me pretty bad in a couple of places, for instance. It wasn’t until we had her tied up and gagged that she finally stopped resisting. But we wasted a lot of time.”

“I see. Did everyone take part?” He looked pointedly at Amy, who was in the middle of taking Alan’s shirt and pants off so he could be as naked as she was. Amy’s love of nudity was growing stronger by the day. Sometimes, she almost seemed offended when the loved ones around her were still clothed.

Amy answered, a bit embarrassed, “It was kind of fun.”

As that answered Alan’s question, he asked Janice, “And since then?”

Janice hung her head in defeat. “Not good. It’s like I said. She really resents us trying to usurp her authority. Plus, none of us have the same connection with her that you do. I’m not even sure what we’re supposed to do. I’ve led the way with a lot of spanking, on an already red and inflamed ass I should point out, but if anything she seems to enjoy it. Simone told us ‘no mercy,’ but it’s not like we’re expert torturers or anything. I’ll admit, it’s been fun. But every time we remove her gag to see if she’s ready to confess, she just taunts us with insults.”

“Hmmm.” Alan pondered. He held his chin in his hand, acting for all the world as if he wasn’t getting blown quite intently by Kim. Then he said, “Well, you tried. Janice, let’s see a titfuck from you, and Joy, you take my ass.”

Kim pulled her mouth off of his erection, feeling very disappointed. “What about me? Don’t you like me anymore?”

As Amy hugged Alan from the back and rubbed her tits into his skin, Alan said calmly, “Kim, of course I like you. I didn’t want you to stop. Please fondle my balls from below. But I really need to cum before I can get started with Heather, and I’m in the mood for a titfuck from Janice.”N0v3l–B1n was the first platform to present this chapter.

Kim, Janice, and Joy took their positions on their knees around Alan. Janice led the way, usually sliding his big rod between her boobs with short strokes so she could flicker the tip of her tongue on the tip of his penis at the same time.

With a nod from Alan, Amy went back to where she’d been sitting before Alan came in. She looked disappointed but she didn’t complain. She sat above Heather, who was lying on her stomach. With the others all preoccupied with Alan’s privates, it was up to Amy to keep pumping one large dildo into Heather’s ass and another into her pussy.

Alan mumbled, “This won’t take long.”

Heather was extremely annoyed that she couldn’t watch, much less take part. Amateurs! Pathetic, the whole lot of them! My tits are much bigger AND better! I should be titfucking him right now. Traitors! Back-stabbers! God, Janice isn’t even sucking on the tip. FOOL!

Sure enough, within a minute he tensed up and decided to stop fighting the release.

Kim, holding his balls, could feel them tightening, and she jokingly shouted, “Thar he blows!”

Janice bent forward and took the head of his penis in her mouth. As a result, his unusually large load was entirely swallowed by the feisty redhead.

“Tastes good, huh?” Kim asked Janice.

Janice still had some cum in her mouth, and she swilled it around, savoring the taste. “Yeah. Surprisingly good, in fact. It’s weird how it’s so sweet.”

Heather was pissed at all that too. UGH! Such incompetence! They made Sir cum way too soon! That’s nothing by his standards. And then Janice gets rewarded with a cum load in her mouth?! It’s an outrage!

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This content is taken from 𝑖𝘦.𝒸𝘰𝑚