6 Times a Day

DM [ 5 / 5 ]

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Alan took his much needed nap once the “cleaning” was done. He was exhausted from two days of extra tennis, not to mention all his sexual activity, so he figured he would sleep a long time.

But while he was sleeping, the front doorbell rang and Susan went to see who it was. Guests were so rare and unexpected lately that she had to change quickly from her robe into some more respectable clothes grabbed from the underwear cabinet.

Susan opened the door and saw Heather standing there. They’d never spoken to each other before, but Susan knew of her and recognized her, particularly now that Katherine and Amy were part of the cheerleaders that she led. Susan had heard a lot of unfavorable gossip about Heather, but still knew nothing of her recent sexual antics with Alan or anything about body-painting “panties” on the cheerleaders.

She was momentarily shocked at the way Heather was dressed: tight short shorts and a white top so small that it was left to the bra underneath to cover up some of her ample boobs. But then Susan remembered hearing that this was how Heather always dressed. The head cheerleader was locally famous for her looks and the way she flaunted them.

“Hi, Mrs. Plummer,” the young bombshell said. “Is Alan at home? We have plans to study together this afternoon.” Recalling her last beach encounter with him, she added as a private joke to herself, “It’s a cram session.”

“Oh,” Susan said, chagrined. Having a guest over meant everyone had to behave completely normally until that person left, and she wasn’t happy about that – especially on a Tuesday. But she did her best to hide her dismay. In a happier voice, she went on, “Oh hi, Heather. He’s here, but I’m afraid that he’s taking a nap.”

Heather looked at her watch. “This is the time we’re supposed to start studying. It’s for a class project; it’s really important stuff. I’d better go and check if he’s up yet. I’m sure he set his alarm or something, ‘cos he knew I’d be coming at this time.”

Susan looked at her dumbly when what Heather was saying sank in. “Study? You two are going to study? TODAY?!”

Heather looked at her a bit puzzled. “Uh, yea-ah. Is there a problem with that?”

Susan felt crushed. Oh, poo! How can I suck my Tiger’s big fat member when SHE’S here? Doesn’t he know it’s Tuesday? Doesn’t he want to play with me all afternoon? I know he has to take his nap, but I thought I could suck his cock for an hour or two after that.

On the other hand, maybe he’s trying to be responsible. He does have to study, even on Tuesdays. And he said this is a tough week. Maybe he has some stuff due tomorrow. I wish he would have told me, though.

She suppressed a heavy sigh and put a smile on her face. “Oh. Okay. Come on in. Would you like something to drink or eat?” She led Heather into the interior of the house.

“No thanks. I want to make the most of our study time together. I’ll just go check on him now, if that’s okay.”

“Sure thing. Up the stairs, turn left, first door on the right.”

“Thanks! By the way, nice house.” Heather hadn’t known that Alan lived in what was almost a mansion, with a big pool in the backyard, because he’d always dressed modestly and, for reasons Heather couldn’t understand, neither he nor Katherine had their own cars or cell phones.

As Heather walked away, wiggling her tightly clad ass, Susan fretted. Oh dear. How can I compete with that young bit of fluff?

Susan, in her modesty, didn’t realize that she was even more attractive than Heather. I hope Tiger doesn’t spend his Tuesday afternoon lusting after that girl instead of me. With the way she’s dressed, he’s bound to get a hard-on, and then there won’t be anyone available to help him out! Oh no! He might have to go for hours as hard as a steel bar while they are trying to do homework together, and there’s nothing I can do about it. Poor dear!

Heather had recently peppered Katherine and Kim with questions about Alan, enabling her to gradually figure out details of his life, such as the fact that he took a nap almost every afternoon. (Getting more energy so he wouldn’t have to take such naps was the supposed purpose of his unusual medical treatments, but there hadn’t been any apparent impact on his nap habit so far.) Heather had timed her visit to catch him in bed, and she did.

She walked into Alan’s room without knocking and found him still dozing. Of course they hadn’t planned a study session, as Heather never studied; that was just an excuse to get past his mother. She carefully pulled back his covers without waking him, and saw to her delight that he was sleeping naked. Better yet, his dick was fully erect.

Confident that he’d love what she was planning on doing, she removed her top and bra. Then she got between his legs and began stroking his boner. Within a minute or so, the stimulation provided by her hands caused him to wake.

“Who? … What? …” He looked up. “HEATHER?!” He was so surprised to see her there that he practically screamed her name at the top of his lungs.

“Shhhh,” she said. “We’re supposed to be studying together.”

“Heather! Oh my God! You can’t be here. This isn’t happening!”

“I am, and it is.” She giggled. “What’s the problem? You don’t like being woken this way? Any other guy in school would kill to have me do this to them, but today I picked you. So enjoy it.” She went back to stroking his rod.

He couldn’t help his first thought: Wow! Woken up by a sex act twice in one day. And by my mother and the head cheerleader! Oh my God, and she’s nearly naked!

But even as he began to feel exquisite pleasures through his prick, he started to think of all the reasons why Heather being there was a bad idea. We could get caught. I’ll bet the door isn’t locked. Anyone could come in. Or someone could overhear. Chances are someone WILL come in within the next hour. Perhaps Aunt Suzy will come by, if only to check on my orgasm chart. Shit! What if I’d said Aunt Suzy’s name, or even worse, my mother’s or sister’s name, before I saw it was Heather?

My God, the possibilities for Heather finding out that I’m making it with my family are almost limitless! For instance, what if she’d come to the house an hour earlier, while Mom was giving me that blowjob? It’s total luck that I aired out this room somewhat, because the whole place smelled like an ocean of cum. Oh my God! She could even look at the orgasm chart on the back of my door! We just can’t have strangers in this house. I’ve got to get her out, and fast!

Heather suddenly stopping jacking his dick and stood up next to the bed. “Don’t worry; I didn’t come here to give you a handjob.”

“You didn’t?” he asked, suddenly disappointed that she’d stopped, even though he’d just been trying to figure out how to get her to stop.

“Of course not. Not when I can have you fuck me instead.” As she said this, she squeezed out of her tight shorts, revealing that she wore nothing underneath.

But even as he watched her get completely naked, a new sense of fear washed through him. He said in a soft but determined voice, “No! We can’t do that! You shouldn’t have come here uninvited. It’s a bad idea – a really bad idea. I’m sorry, but you have to go.”

He wondered how he could create a distraction and take the orgasm chart down before she noticed it. It was clearly labeled: “My Daily Orgasms”. He was afraid to even glance toward it for fear his gaze would draw it to her attention.

She put her hands on her bare hips and said testily, “Alan, just what the hell is wrong with you? The most beautiful girl in school is standing here practically begging you to fuck her, and you just say ‘No thanks. Get lost’? You’re really starting to bug me. I thought we had a really good time at my house after Baskin-Robbins, and I expected you to come back for more. But it’s been, like, a week, and you haven’t. I feel gypped after meeting you at the beach over the weekend and not being able to do it again. I KNOW you wanted to do me then. We’re long overdue for another fucking. I came here ‘cos I wanted to give you a good, long fuck. But this is the response I get? Are you gay or something? Do nerds not like fucking real girls? Seriously!”

Alan remembered Suzanne’s advice to play hard-to-get with Heather. But he also knew he couldn’t have Heather turn against him. She was difficult enough to deal with when she was happy; he hated to imagine how awful she would be if she were vengeful. “No, Heather, it’s not like that. You’re one of the most beautiful girls in school and, God, I’d love to fuck you. But I have to be really careful. I’m willing to fuck. Let’s do it, but somewhere else. We can go to your house right now. But no way can we do it here. My room is like Grand Central Station. People come and go all the time without knocking. I can’t afford to get caught!”

She felt slightly better about that, but still asked, “So then why haven’t you come to my house then? I told you, you could come in the back window any time, day or night.”

He couldn’t tell her the main reasons: that she really scared him with all her power games and her love of risk, and that the other women in his life were keeping him so constantly satisfied that he had no need of her. But he could tell her a less important and still honest reason. “Can’t you see I’m chicken when it comes to getting caught? You said your dad was like a body builder and would crush me if he saw me.”

“Did I say that?” She smiled, delighted.

It seemed to Alan that she relished the memory of scaring him.

“Oh yeah, I guess I did. Well, he’s a big, strong guy, a former Marine officer. I’m disappointed in you. What’s life without a little risk? Besides, I live a charmed life; I never get caught at anything. I’m sure we can fuck right now, since I’m already here, and it will be just fine. Relax.” She made a move to crawl back onto his bed, but he got in the way.

“No. Really! You may live a charmed life, but I don’t.” Even as he said this, it occurred to him how wrong that assessment was. Actually, I’ve probably got the luckiest, most charmed life on the planet, at least for these last few weeks. But that’s beside the point. Heather could still ruin everything. My luck can’t last forever.

Knowing that she wasn’t going to leave unsatisfied, he suggested, “Let’s go to some remote park or some place like that, and do it there. No way can we do it here; it’s far too dangerous!”

His saying “too dangerous” turned out to be a big mistake: it was like throwing a juicy T-bone steak in front of a hungry dog. She practically clapped her hands together in glee. “Alan, we’re gonna do it here, and that’s final. We can be very quiet and put a chair in front of the door or something.”

She got up and moved a chair to block the door.

He used those precious seconds to put on some clothes and sit on a chair away from the bed. He breathed a huge sigh of relief that she was so busy looking at fitting the chair under the door handle that she missed examining the orgasm chart just a foot or so higher on the door.

When she turned around and saw him just sitting there, clothed, she was disappointed and frustrated. But having a guy actually not show interest was so rare that it only turned her on even more. “Damn you! What do I have to do already to get you to fuck me?” she pouted.

“There’s nothing you can say or do. Sorry. Somewhere else, okay; I’d love that. But not here, and especially not now. I mean it.” He crossed him arms and looked away from her defiantly.

Heather turned on her most sultry voice. “Alan! You can’t say no,” she moaned softly, as if she were at the heights of orgasm. “You see, I have this problem.” She got down on the floor right below his chair and spread her legs wide.

“Look Alan. I have an itch. It’s a very nasty itch.”

He couldn’t help but turn and look at her toned and deeply tanned nude body.

She purred, “Do you know where my itch is? Do you know where I’m feeling so nasty? It’s in my pussy. My pussy is on fire! It itches like poison ivy. It’s sooooooo bad. It needs you to put it out.”

Her legs began twitching and she started to writhe on the floor, as if she wasn’t in control of her body but the itch had taken control.

He wanted to turn away again, but he stared, completely transfixed.

She moaned sexily, “There’s only one thing that can satisfy it. It has to be something hard. And long. And thick. And hot. And meaty! To reach my itch, deep, deep inside my cunt. Only you can reach it, Alan! Only your incredible cock. So hard and long. It’s the biggest and the best. You’re the best fucker I’ve ever had! You have to help me. Please, I’m begging you! Fuck me. Otherwise I’m going to die! This itch is killing me! Scratch it, in and out, in and out, in and out, with your big dick! Fuck me now, please!”

She kicked her legs up in the air, then pulled them back over her head and presented her slit to Alan in the ultimate position of supplication.

He thought, My God, man! This is Heather, supposedly the most desirable girl in school! She’s stretching out her sexy, naked body on my floor, begging me to fuck her! And I can’t! I can’t! Forget playing hard to get; I’ve done enough of that for now. I’m soooo ready to fuck the living shit out of her! It’s just that I’ve gotta get her out of the house, and fast!

She stopped moaning and writhing long enough to steal a glance at him and see if her performance was working. One look at his crotch left no doubt that his dick was straining for relief, but still he sat immobile in his chair.

“Alan!” she said in a far less sexy voice, now with incredible exasperation. “This is a grade-A performance here! That would have made the dick on a marble statue erupt, for crying out loud. What do I have to do? Don’t you want to fuck me already?!”

It was all he could do not to just jump up and take her. He could feel his resolve slipping rapidly. Suzanne’s recent words of advice about Heather came back to him: “If she wants to fuck you again, she will. If she goes all out to tempt you, you won’t be able to resist.” Man, that is so true! I’m a goner. But still, she doesn’t know that yet. If I can hold out a little bit longer, at least I might be able to win something.

He kept his cool long enough to say, “I do. But only on one condition.”

“What, already?”

“That you don’t ever, ever come back here again unannounced. We can do it anywhere and everywhere else, just not in this house. My mother is such a prude that it’s not even funny. If she caught me, she would literally kill me, and I’m not going to take that risk.” He thought back ironically to the blowjob that his mother had given him just before his nap.

Heather already knew about Susan’s prudish reputation, since she’d been asking around about Alan and learning more about him and his family. “Okay, okay. I promise. Now fucking scratch my itch! Do it!”

“And…” he continued. He figured they were in a battle of wills, and he was winning by having more self-control. He thought, What else do I want from her? She already wants to fuck at the drop of a hat. What else do I want? Oh I know. He added, “And one more thing. You have to do anything sexual that I want, at any time.”

She rolled her eyes. She couldn’t imagine anything that this mild-mannered, polite guy would want her to do sexually that she wouldn’t like doing in the first place. “Fine. Whatever. Just fuck me, like, yesterday!”

“That includes blowjobs,” he reminded her, knowing that she hated to do those. 𝘯𝑜𝘷𝑙．𝑐𝘰𝘮

“Oh fuck. Whatever. Just do me!” She was ready to promise him anything, since she only kept promises when she felt like it.

“Wait. I want to hear you say it.”

“Say what?”

“Your promise.”

Her entire body was vibrating with need. She growled angrily, but then said, “Fine! You can do anything you want to me at any time. Including getting blowjobs. And I damn well hope you do, starting right fucking now!”

She found it strange that saying that turned her on so greatly. No boy had ever made demands on her like that, much less been successful in doing so.