6 Times a Day

Chapter 256 Alan And Heather Bantering [DD Sponsored]



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They lazed around on her bed and chatted while they waited for him to get hard again. Their mood was different, without any meanness or name-calling. In fact, they talked mostly about innocuous things, such as the decor of her room.

Alan’s anger and frustration gradually dissipated, restoring him to his usual mild-mannered self, somewhat like the transformation between Dr. Jekyll and Mr. Hyde. However, Suzanne’s recent advice came to mind again and he was careful not to be fawning or even complimentary, instead projecting a hard-to-get attitude. Even when she went fishing for a compliment about what a great fuck she was, he didn’t say much.

That intrigued and challenged her. She was already thinking about what she could do differently next time to really impress him.

As he lay there next to her, he suddenly realized how much time had passed and asked, “Aren’t you going to be late for the matinee with your boyfriend? It must have started already.”

“Oh that? Who cares?” she answered blithely. “This is so much more fun. I’ll make up some excuse about missing him. He’s well-named; he’s dumb as a rock, so it doesn’t matter what I say.”

However, Alan tensed up. “But what if he comes here to look for you? Isn’t that pretty likely? And then he’ll find me in your bed!”

“Could be,” she said, seemingly more delighted at the idea than worried about it. “But you should be even more worried about my dad. If you think Rock could beat you up, you should see him. He’s a huge former Marine!”

“Thanks for the news,” Alan said ruefully. His pulse quickened with fear.

As if happy about his potential misfortune, she added, “Yeah, and it’s getting near five so my parents should be back any time now.”

“Shit!” he bolted out of bed. “Now I’ve really got to go!”

“Reeeeelllaaaaaxxxx…” She grabbed him and pulled him back down on the bed. She was in the driver’s seat now and wanted to have more fun with him. “That’s what the back exit through the window is for. Just walk onto the roof, climb down the tree, and you’re gone. Believe me, lots of guys have found it very useful. But now, let’s do it again!”

The mention of “lots of guys” reminded him of Glory’s warning that Heather was probably a cauldron of STDs. Rather timidly, he asked, “Hey, uh, do you have any, you know, diseases?”

She laughed. “You ask me now, after we fuck? No. I’m incredibly charmed in all things sexual. I swear to God. So let’s get it on. Of course I’m on the pill. But if you insist on wearing a condom, I don’t care.”

“Okay. I’ll get another one.”

That surprised Heather. She’d actually thought they were all done, so had already stood up and put her top back on. She’d been speaking in general but was delighted that he was talking about getting it on again immediately. “What? You’re really ready for another round?”

He answered honestly, “I think so. I mean, I’ve only cum twice. Most days, I cum about six times. Sometimes more.”

She was stunned. Holy shit! Kim, I could kiss you for finding this jewel in the rough! If my supposedly studly boyfriend Rock cums twice in one evening, that’s a big deal – I’m supposed to break out the balloons and party hats. Most of my other male lovers have been no better. No wonder I’ve started to play around with women more and more. Maybe I’ve been barking up the wrong tree by sleeping mostly with hunky football players. Maybe brains do matter.

God, what if it turns out that nerds are all well-hung studs and the jocks have the tiny dicks?! What a nightmare world that would be!

She finally just responded, “But three times in one hour? Are you sure you can do that?”

“I can’t guarantee anything, but I’ve done it before. I’ll tell you what. Maybe, if you could suck on it a little bit, I might revive.”

“You want me to give you a blowjob? Ha! Fat chance. That’s gross and demeaning. Besides, I don’t like the taste of cum.” She didn’t give the primary reason why she didn’t like giving blowjobs: she was selfish and didn’t like to do anything sexual that the other person enjoyed more than she did.

He was tempted to boast about the taste of his cum, but was too modest to do so. Instead, he said, “What if we compromise? How about if you give me a titfuck? That should get me started, and then we can switch once I’m fully up.”

She frowned. “Hmmm. I’m not exactly crazy about that idea either. But today’s your lucky day. Okay, just a little. Consider it a reward for some excellent fucking.” She wouldn’t have gone for it except that his playing-hard-to-get approach was having an effect on her.

She got some lotion from her dresser and lathered up her cleavage. Then she knelt down in front of him and put his semi-erect penis between her generous jugs.

“Oh maaaaan, I really shouldn’t be doing this,” he said out loud as she began to massage his dick back to life with her large silicone-enhanced breasts.

He could tell she had implants by their feel, but he didn’t care. He figured that her boob job must have been unusually costly, because they looked and felt really great. It was hard to tell the difference; only his recent extensive experience with a variety of breasts tipped him off.

The two of them continued silently in a nice titfucking rhythm for a couple of minutes.

Then, more to himself than to Heather, he said, “Titfucking is my homework assignment.” He was thinking back to his first titfuck with Akami the previous Friday and how she had told him that he needed to practice what he’d learned before his next appointment with her. He was amazed that, just a few days earlier, he hadn’t really known anything about how to titfuck, but now he was going at it with Heather as if he’d been doing it for years.

Figuring it was some attempt at a joke, she answered, “Well, then, let’s make sure you get an A plus. Fucking stroke your big shaft right between my monsters. Like that! Good. Don’t you just love my tits?” She cupped them with her hands to make them stick out even further. She didn’t exactly have a modesty problem.

“They’re great,” he admitted. While it was true he adored all-natural boobs like Susan’s and Suzanne’s even more, augmented boobs like these were still great fun to play with. But then he remembered he shouldn’t praise her too much, so he added, “That is, considering that they’re enhanced.”

She didn’t answer that, since she sensed he wouldn’t believe her if she lied about them.

To her surprise, she found herself getting so horny that she said with genuine feeling, “Mmmm. Alan, your dick feels so HOT. You’re on fire, making my tits burn up. It’s so raging hard and boiling hot!”

He liked that, so he ran with the idea. “Put my fire out by smothering it with your big tits, you sleazy tramp!”

That made her even more excited. “I will! I will! Fuck my tits hard! Cover them with your sticky jizz!”

He pounded up and down her cleavage. She bounced her body up and down as well, so his shaft practically flew through her tight, well-lubed channel.

Heather had rarely deigned to allow any man to titfuck her. Despite her extensive sexual experience, it had mostly been fairly standard missionary-position or doggy-style intercourse with men, or pussy licking and strap-on dildos with women. But, perhaps for the first time, she found herself really loving getting titfucked. She realized that it wasn’t just something to do to get a dick hard before intercourse; she was getting off on it so much that she wanted to see it through to the end.

There wasn’t much talk this time; both of them had a hard enough time just breathing. She did manage to say, “Keep going! Do it!”

He was very happy to oblige. The fact that her cleavage was so thoroughly lathered up with lotion made the titfuck especially pleasurable. Furthermore, since her tits were extra firm from her boob job, and since they were so large, she made an extremely excellent tunnel for his erection to fuck. When she pressed her boobs together, it very nearly did feel like he was screwing a tight cunt.

When he came, his seed arced toward her head. Both of them screamed for joy.

He was amused at how much landed in her hair and even on the top of her head. To his surprise, she didn’t mind, and even seemed to revel in getting sprayed by cum everywhere.

He might have lost his load, but he hadn’t lost his attitude. Inspired by the way his cum had fallen all over her face and chest, he resumed his acting. With both of his hands on top of her head, he pushed her face down into her chest.

Initially that alarmed her. She protested, “What are you doing? Don’t make me eat that stuff. Cum is disgusting!”

But he would not be dissuaded. He understood that most cum was bitter or sour tasting and that she mistakenly assumed his was like that. He figured that if he was unable to praise his own seed with words, he’d just have to get her to see how good it tasted some other way. So he continued to push her and “forced” her to lick up as much of his cum as she could find. “Take it, bitch! Eat it all!”

“No!” she protested, even as she licked up a big gob from the top of her left breast. She didn’t like the idea of eating his cum, but she loved the way he was treating her.

“Are you a slut, or what? Sluts live on this stuff! Eat it up! All of it!”

“Never!” But she still ate more. In fact the more he prodded her with rude words, the more eagerly she went after every last drop.

She loved the treatment so much that it took some moments before she began to realize that she was enjoying the taste of his cum as well.

When it was all over and she’d cleaned up all the cum except the gobs that had landed in her hair, she had to admit, “Alan, I never thought I’d say this to anyone, but I actually like the taste of your spunk. You have to understand that normally I HATE cum. It gets everywhere. It’s disgusting and gooey. And the taste. Yuck! That’s the worst. But this is completely different. It’s like… dessert. Seriously! Some women – their juices I can tolerate. Barely. But this… I want more!”

He finally let his modesty slip a bit. He was bursting with pride that Heather had been proven wrong about his sexual skills. He was particularly miffed at her comments at the beach about him being a virgin, so he said, “That’s what a lot of women say.”

“A LOT of women? Alan, just a couple of days ago I thought you were a completely hopeless virgin nerd. If you’d kissed a girl before, you could have fooled me. You’re telling me you’ve been with a number of women? Who?!”

He realized he could use her slip-up to his advantage. In particular, he thought about how Suzanne had told him that she’d convinced Brenda that he had many other lovers, without actually giving any specifics. So he ‘confirmed’ that he had many other lovers with the vague comment, “Sorry, I don’t kiss and tell. I’ve probably said too much already.”

“Kim did say you were discreet. Chalk up another point for her, and for you! I love it. We really have to do this again soon. I never would have figured. Where the hell did a nerd like you learn to fuck like that?”

“Hey, I don’t appreciate being called a nerd all the time. For one thing, if I’m such a nerd, then why would Miss Social Princess here be fucking me in the first place?”

“Good point. Okay, I’ll admit you’re not a typical nerd. And you’re certainly a lot better looking and more muscular than the typical nerd, I guess ‘cos you play sports. But you hang out with dweeby guys and get good grades, so that makes you a nerd.”

“That still begs the question. Why did you shanghai me today, if I’m such a dweeb? And what’s with all this stuff about Kim?”

“Okay, you’re not a dweeb, exactly. Happy? I’m just pointing out that you should find a better crowd. It would look bad for me to be seen with you at school. The reason why you’re here is because of Kim. She seems to think you’re the best fucker on Earth. Earlier today at school she was raving and carrying on and on about you. She said you don’t just do wham-bam five-minute lovemaking, but really take your time and pleasure the woman.”

She continued, “I figured if you can get someone who’s a lesbian that excited, I had to try you out for myself. If I hadn’t lucked into you at the ice cream store, you would have heard from me soon enough, one way or another.”

“Huh. So you’ll fuck a nerd based on some gossip?”

“Not exactly. I have to admit, there was something about you that intrigued me the one time we met. Oh, and then there’s that big bulge you were showing off there at the beach.” She patted his groin with fondness.

“Hey, I wasn’t showing it off. That happens. Sometimes guys can’t control it.”

“Yeah, right. Show-off!” She teased him, but playfully. “I gotta admit, you surprised me. I can’t believe I’m lying here naked with a nerd, let alone having such a fucking good time. This is just like that Revenge of the Nerds movie where that total loser guy with the glasses gets the girl.” She quickly corrected herself, “Except that you’re not a total loser, and you don’t have glasses.”

He was annoyed. “What’s with you and nerds? You know, just because someone is smart doesn’t mean you have to shun them. I can tell you’re pretty smart yourself, even though you obviously don’t study much. Or at all, I’d guess.”

“I’ll admit it. My goal is to be popular and have fun. If I pass my classes too, that’s a nice bonus. Okay, I’ll try not to call you the ‘N’ word so much. But you never did answer my question. How did you learn to fuck so well?”

In a confessional voice, he admitted, “To be honest, I haven’t really done it much. You’re my third.” He immediately regretted saying that. He instinctively knew that with Heather one should never admit weakness. He felt like kicking himself, because it undercut his attempt to convince her that he wasn’t impressed by her due to all his other lovers.

But she took it pretty well. “The third time?! Talk about a natural. All that name calling and stuff just came to you spontaneously?”

He nodded. “You’re the third woman I’ve actually fucked. But I’ve played around with many others. You know, blowjobs, titfucks, handjobs – that kind of thing. Lots of women love to suck my cock. That’s why I said women like the taste of my cum. I just haven’t gone all the way that much.”

He thought, Good. That kind of fixes my slip-up. Mostly. Besides, it’s basically the truth.

She considered that. “Huh. Still. Most guys I have sex with never learn that I like that. Who was your first? It wasn’t Kim; she told me that. She must be your second, and she’s totally inexperienced with intercourse too. I want to shake the hand of your first for making you such a pro fucker so fast.”

He avoided the question and changed the subject, since his first was his sister. He thought, Thanks, Sis. And thank you, Kim and your big mouth. Although, now that I think about it, Aunt Suzy was really the one most responsible for making me at ease and so creative sexually.

He said, “Kim talks too much! You’re not so bad yourself. And I’ve gotta admit you really know how to keep your body in shape.” While he was being honest, he also had the ulterior motive of changing the topic from the identity of his first lover.

It worked like a charm. There was nothing Heather liked to talk about more than how beautiful and fit she was. She delivered a monologue about her exercise regimen.

But after that, the conversation petered out and never really resumed. He found that making polite conversation with Heather was very awkward. The two of them had very little in common, and the nerd / queen social divide was painfully obvious. The only reason to stay was more sex, but he knew that he couldn’t get it up again. 𝐞𝐨𝘃𝐞𝐥.

She realized this and felt the need to find Rock before he got too angry. She made Alan feel like he’d overstayed his welcome.

The fact that her parents were supposed to come home at any moment was also on his mind, so he finally got up and left.

As he drove away, he wondered at the remarkable experience he’d just had. He thought it unlikely to ever be repeated because, while she’d dropped some heavy hints that she’d like to get fucked by him again, she seemed to become disinterested when he was preparing to leave. Furthermore, she’d stressed repeatedly the need for him not to mention what happened to anyone. More insultingly, she’d warned him not to act friendly to her at school. She’d even said, “Sorry, no offense, but I just can’t afford to be seen talking to a nerd. It would ruin my image.”

He felt a little bit used, but all in all he couldn’t complain. It had been a wild, fun ride, topped off by some truly great sex. Plus, it really did seem like an advanced test to get him ready to face Brenda. He thought, Heather is fucking intimidating. She really is. Not just looks, but personality. But I totally rolled with the punches. Compared to her, Brenda will actually be easier! And I just fucked Heather, whereas all I have to do with Brenda tomorrow is talk to her. Piece of cake!

Boy, I can’t wait to tell Aunt Suzy! She’ll be so proud. Oh, wait. I can’t kiss and tell. Besides, if she knew I had sex with Heather, she’d get upset and give me an earful. Damn! I’ll just have to impress her with how I interact with Brenda tomorrow.

As to being used, he figured he’d gotten off easy. He realized that Rock was less Heather’s boyfriend and more a dumb chump whom she constantly delighted in cheating on in the most outrageous ways. He gathered that her picking up strange guys practically in her boyfriend’s face, like she’d done with him at the Baskin-Robbins, wasn’t all that uncommon.

In fact, in retrospect he realized she’d seemed surprisingly trusting with him, actually gloating to him about her cheating. She’d even mentioned that her favorite trick was to talk to Rock on the phone while she was having sex with one of his football buddies.

Alan felt genuinely sorry for the guy. But at the same time, he had to admit to himself that the danger of getting beaten up by Rock or by Heather’s father helped to make the sex even more arousing.

That was GREAT sex. But dammit, it was kind of a scary trial too! As good as that felt, I actually kinda hope that’ll be the end of it. If I see her coming directly towards me, I’m gonna run like hell in the other direction before she gets me murdered!

Okay, maybe not, but almost. She’s real trouble, that’s for sure.

Another thought occurred to him. Everything is soooo sexual all of a sudden. I can’t even get ice cream with a friend without something like this happening! Dang, that is weird. It’s almost comical how these things keep happening to me.


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