6 Times a Day



Finally, after nearly a minute, Alan heard Heather say, "Okay, you can look!"

He removed his hand and opened his eyes. Heather was standing right in front of where he was lying down, totally nude but with both hands covering her pussy mound. Simone stood off to the side, also nude, but clearly trying to be inconspicuous. The focus was obviously supposed to be on Heather and whatever her hands were covering.

Adding to the mystery, Heather was blushing, looking very shy and bashful. He'd already figured out that she hardly ever blushed, even when he put her in very embarrassing situations.

Seeing that she had his undivided attention, Heather removed her hands, revealing that her bush had been completely shaved since he'd seen it last. She spoke nervously, "Voilà!"

Alan was at a loss over what to think or say. In truth, he didn't have a strong preference between hairy pussies and shaved ones. He liked variety. It took him a few moments to remember that he'd ordered her to shave her bush off on Friday. Huh. How the heck am I supposed to react to that?! When I told her to shave it off, I didn't think she'd actually do it. I was kind of hoping she wouldn't, so I'd get a new point of leverage, allowing me to complain that she's just too difficult and disobedient to deal with. But then she up and surprises me by doing it!

Since he was lying down on a mattress at the edge of the stage and she was standing right in front of him off the stage, her pussy was only a foot or so away from his face. He gave it a long look, and then looked up at her face. To his surprise, not only was she blushing, she clearly was anxious and hoping for his approval.

He thought, Shit! Now what? If I want to get really Machiavellian, I should be cruel and uncaring, and just say "Whatever" or something like that. But it's hard for me to be that kind of guy. Look at her! This means a lot to her. How can I be mean to her, not in a sex game kind of way, but in a real, hurtful way? But then again, if I praise and compliment her, that'll only encourage her and I'll end up making more of an emotional bond with her.

Dang, this is tough! There's no easy way out. Maybe I'll try to split the middle. I'll compliment her, but only a little bit.

It had taken him about ten seconds to think of what to say, and Heather had been slowly dying of anticipation. Finally, he looked back up to her face and smiled. "It's nice!"

Heather let out a sigh of relief. But that quickly turned to frustration. "'Nice?!' Is that all you have to say?! 'Nice?!'"

He thought, Crap. I guess that wasn't complimentary enough. He said, "Sorry. You caught me at a bad time. I'm half dead and my brain is kind of running on fumes. Let me take a closer look." He reached out with one hand and ran his fingers all over her shaved skin. But he also used his thumb to rub against her pussy lips.

That caused Heather to relax and even smile. She was disappointed by his words, but she could feel his interest in his touch. Plus, she just loved the sensation of being fondled there. She started lubricating rapidly.

He said, "I'm too tired to put it into words, but I do appreciate the gesture."

Heather relaxed and smiled even more upon hearing that. Aaaah! Now that's the Alan that I know and love! Wait, did I just say "love." Shit! I don't mean 'love love', I just mean, you know... the guy I appreciate and lust for. Anyway, what he can't say with words, he's saying with his hand!

Indeed, he was happy to continue fondling her pussy mound. He did explore her smooth, shaved skin, but mostly he focused on diddling her slit and clit. That was getting her very hot and bothered.

Yet, even as he was enjoying doing that, he thought, Shit. I'm not really handling this well. I'm just not bringing my A game today, and one always has to be on one's A game when it comes to Heather! It's probably better if I don't say much at all, instead of likely saying the wrong thing. At least she seems satisfied. I kind of rue ever telling her to shave her bush, but this kind of thing keeps happening. The more I try to keep her at a distance, the more I somehow get sucked in.

Heather was mostly mollified. Finally! I've been waiting three days to show him that I shaved my pussy, just for him, and all I get is a "nice." Okay, more than a "nice," but still, it's kind of a letdown compared to my fantasies. I guess it is bad timing; he does look like something the cat dragged in. But, if I know him at all, and I'm pretty sure I do, once his libido gets charged up he'll turn into a fuck machine! I don't much care if he's not very articulate today, so long as he fucks me like only he can!

With that in mind, Heather was eager to do whatever it took to revive him. Simone was just getting bored, since she was forced to stand silent and let Heather get all the attention. So both girls were happy to get back to massaging him.

Alan kept his hands at his sides and his eyes closed, and tuned out for a little bit.

Heather soon began vigorously massaging Alan's thigh muscles, which were quite tight.

He groaned, "Oh God! That feels so good. Better than sex. My legs really hurt."

She asked, "Just what did you DO this weekend, Alan? And why did you miss your first three classes? I was looking for you everywhere."

"I'd rather not talk about it right now. As you've noticed, I'm not in the talking mood. Heather, why don't you tell me about your weekend? What did you do?"

Heather quickly replied, "Oh, not much." Then she glared at Simone with a look that essentially said, "Don't you dare tell him differently, or I'll kill you!"

Simone wisely stayed silent. But she thought, It's not like I need to tell Alan that Heather was pining for him all weekend, since her behavior today has basically confirmed that anyway. I'm glad that she's finally shown him her shaved pussy, so she can stop going on and on about it. Sheesh! I remember her proudly declaring that today would be the day she would take control of her relationship with him and turn him into her "boy toy." Yeah, right! Already, we're giving him a massage like he's royalty. I think Heather's so eager to get fucked that she's willing to do whatever he says. After that itch gets scratched though, it's anyone's guess what she'll say or do next.

Alan asked, "What's the latest with the football players?"

Heather replied, "Ah. Glad you asked. You said that this weekend was my last chance at sexual freedom and that I should use it to my fullest, so I did."

Actually, that wasn't true. The only sex she'd had over the weekend was with Simone. Having sex with other guys just didn't do it for her anymore, and she knew it. But she didn't want Alan to get a big head, as that would give him even more power over her.

She asked, "But what happened to you? You literally fucked until you couldn't walk straight! I'm right, aren't I?"

"All right, you are. Although I did a lot of hiking too."

Simone asked, "How is that possible?! You were with the Boy Scouts the whole weekend, right?"

"Almost. I was until Sunday night. Then I got back and made up for lost time with a big orgy."

Heather clenched her teeth and growled. Instantly, she was pissed off that she hadn't been invited.

He heard the growl and responded, "You're hardly the only girl I fuck, you know. You're not even close to consideration for membership in my harem, thanks to your attitude. Your half-hearted massaging is a perfect example of why you continue to remain unworthy." He knew that competition was one of Heather's major motivators.

Sure enough, even though she'd finally started giving him a decent massage, she immediately redoubled her effort.

He chuckled to himself. I've gotta keep working that angle. That harem talk seems to both impress her and motivate her. Let's see if I can do a little more of that. He said, "In any case, it's none of your business how many women I fucked last night, or how much bigger their real tits were than your fake ones. Let me hear more about your work with the football team. I hope you aren't a walking disease factory by now."

She was thrown off her game by her desire to outdo these unnamed harem women who were clearly higher in the pecking order than she was. She even let the fake tits comment slide. "I promise you, I didn't fuck any of them. I know how worried you are about the sexual disease thing, so I wouldn't lie about that. All I did was give them handjobs. And good God, it sucked. It didn't seem nearly as much fun to be with them as it used to. My plan was to sow dissent and pit them against each other. For instance, I got the three cornerbacks together and told them that I'd only jerk off the one who was the best player AND the best lover. In that particular case, they started arguing with each other so intensely that I didn't have to do anything with any of them. I think a full-on brawl broke out after I left. Fucking with minds is so much fun!"

That was only partly true. She really had sown dissent among the football players, but only through a series of strategic, clever phone calls on Sunday afternoon. She hadn't given them any handjobs. But she wasn't willing to admit that to Alan, because she wanted him to believe that she was still tempted to have sex with other guys.

Alan was secretly very disappointed to hear that, since he assumed it was true. It annoyed him to hear that she was acting that slutty with the football players, whom he really disliked. He complained, "Heather, this is why you're so far from belonging to my harem, and your idea of being my girlfriend is still a complete non-starter right now. If you try to mess with my mind, I promise you, you will be very, very sorry. And even though you say you only gave 'em handjobs, I don't trust you. For God's sake, I want to see a bill of clean health from a doctor before I get my dick anywhere near your cunt ever again, especially after a weekend like that."

She grumbled, "Whatever. It wasn't easy to hold back from having to do more. But I did it for you, and this is the kind of thanks I get. I'm clean, I swear."

"Well, I hope so. By the way, did you ever have anal sex with anyone else but me?"

Heather paused in her rubbing and hesitated in answering, so Simone whispered rather loudly, "In the end - so to speak - Heather decided that her ass belongs to you and only you."

Heather stopped her massaging to flip Simone the middle finger. "Fuck you! Simone, what kind of friend are you? Why the hell are you telling him all these things?! Whose side are you on, anyways?!"

Alan replied, "Let me answer that, Simone. Heather, Simone is your friend, but she's on MY side when it comes to curing you of your bitchiness. In a sense, that still means she's on your side on that too, because this is all to help you. She's going to be my assistant from now on in this project to fix your personality. Isn't that so, Simone?"

Simone nodded, and said to Heather, "I love you, girl, but Alan seems to know what he's doing, so he gets my full support. It's for your own good."

Both Simone and Heather's hands had been slowly drifting down to Alan's ass. Heather now gave up all pretense of massaging. She reached under him and began an excellent handjob. It seemed his finding out so much about her only turned her on even more.

Heather's position put her face practically in his ass crack, so he decided to push his luck further. He said, "Heather, since your nose is already up my butt, why don't you rim my asshole with your tongue?"

She pulled back in disgust. "What? You've got to be kidding! Not on your life! That's beyond disgusting."

"Oooh, excellent. Something else she hates that I like. I'll have to remember that. But it's not a request, it's an order. Or, let me put it this way: is anyone volunteering to get ass fucked? Say yes by licking my asshole."

Heather feared this would become a new punishment for her, so she tried to use reverse psychology on him. "Actually, I'm just kidding. I love it! You know how much I love asses. I rim Simone all the time, don't I, Simone?"

There was a long pause, and then Simone said, "I'll refrain from answering for fear of getting in any more trouble with either of you." (In truth, that wasn't something Heather ever did for anyone.)

Alan laughed. He decided to pretend to at least entertain Heather's reverse psychology even though he could see right through it. "Heather, I don't care if you like it or not. Do it. Now."

So Heather began to lick his ass crack, but generally refrained from getting near his asshole. She still couldn't bear to do it, even though he was clean down there.

Still, she managed to make Alan feel really good, especially when her tongue focused on the space between his asshole and his penis. Her continuing handjob and Simone's ass cheek groping didn't exactly hurt, either.

She thought, FUCK! This is seriously fucked up! First, he got me to shave off my bush. I wouldn't do that for anybody, not even Simone, but I did it for him. Now he's got me licking his ass crack! Doesn't he know who I am? I'm Heather fucking Morgan! I'm the head cheerleader, the queen bee of this school, the most beautiful girl around! He is a fucking machine, but he's a social nobody and a nerd too. This shouldn't be happening! But when I get my hand on his cock, it's like I can't help myself!

Simone seemed intensely interested to see whether Heather really would rim Alan, so she spread his ass cheeks wide to give herself a better view of what Heather was doing.

The pressure from Simone's constant staring finally forced Heather to put her tongue right on Alan's anus, but she quickly withdrew it.

Simone thought, Wow! Heather really must be in love with him. As she would say, "Heather fucking Morgan doesn't lick anybody's ass." But she's licking his! What a trip this is, getting to watch. So much for her turning him into her "boy toy" today. Ha!

At the same time, Heather thought, UGH! Fucking disgusting! I can't believe I just did that. He damn well better fuck me within an inch of my life today! I deserve it, after that. Yuck! She licked around his anus without touching it again, and kept right on jacking him off.

Alan figured the massage was effectively over since things were heating up. So he sat up, causing both of them to stop what they were doing. He felt a lot better; almost like a new person. His renewed energy gave him more confidence in dealing with Heather. He still didn't feel like he was bringing his A game, but he was getting there.

He said, "Thanks for the massage, gals. Heather, if Simone pisses you off when she helps me, blame me, not her. You got that? She's just following my orders."