6 Times a Day

Chapter 254 First Time With Heather Pt 1

?As soon as Heather got into Alan's car and closed the door, he muttered, "You're insane! Are you trying to get me killed?"

"That was so much fun," she said happily, maintaining a poker face while speaking in a low voice.

Rock watched them as he walked to his car, but then finally turned away.

Heather looked at Alan with concern for the first time. "How are you handling this? Can you deal?"

Alan was determined not to be outdone by Heather. "Yeah, I'm good. I can deal. I can roll with the punches." He had no idea what he was agreeing to.

"Good. That's what Kim told me. I didn't entirely believe her, but I'm glad I decided to find out for myself. I haven't had this much fun in years! Sex with a nerd. Ha! Now take me home and fuck me already."

He couldn't believe his ears. He had a hard time just managing to breathe. It took a moment before he could manage to gasp out, "What?!"

"You heard me," she replied calmly, greatly amused at his obvious panic. Actually, she was a bit surprised at her words as well. She hadn't intended to have sex with him when she'd started teasing him back in the ice cream parlor, but events had their own momentum. Now she was hot to trot and ready for a good fucking. "Can you deal, or what?"

"Yeah... I... can deal."

"Then let's go! My parents are still at work, but we don't have much time. I hope you can drive with my hand on your cock." She unzipped his fly again even before Rock was completely out of sight.

Alan had been in a lot of strange situations in recent weeks, but he considered this to be the most astounding yet. He thought, Holy fuck! At the beach she was talking to Simone like I was some kind of low-life scum. Now she wants to have sex with me?! And she somehow expects me to drive with her hand on my prick?! There's no way! No friggin' way!

But somehow he managed not to crash. He made no attempt to talk, devoting all his attention to his driving.

It wasn't easy to concentrate, though. Heather kept her fingers running up and down his shaft the entire time. Actually she was being very careful, using only limited, light touching, because she didn't want to get in an accident or have him shoot off in the car. However, it sure didn't feel that way to him. The mere fact that she was touching his dick while he was driving, or that she was touching it at all for that matter, was so exciting that he had a constant struggle not to cum.

She didn't try to talk to him much except to tell him when to turn. She found herself getting extremely aroused, even panting heavily with desire.

Somehow, despite all the distractions, he managed to think things over. She said Kim told her I can roll with the punches, and that's true. I can! I honestly don't think this is a prank. If it is, she's the best actress ever, because that look of lust in her eyes can't be faked. If this is for real, I've gotta rise to the occasion. Nerd gets to fuck head cheerleader? How can I not? I'd be letting down all of nerd-dom!

Thank God I have Aunt Suzy on my side. The training she gave me last night so I won't be intimidated by Brenda could work equally well for Heather right now. Why the hell not? In fact, this can be kind of an advanced test to get me even more prepared for Brenda. The key thing is to get in the mode where I feel like I'm an actor in a play. I can't get hurt because nothing is real. It's all kind of a big joke, or a dream. I did it successfully earlier today role-playing with Glory, so I'll just do it again. I can do this!

Heather didn't notice it, but Alan's attitude and even his demeanor changed, due to his new resolve. Even his heavy breathing eased up considerably, because he wasn't feeling so panicky. His urge to cum was reduced as well.

As they got closer, she started to speak: "So... I hear that you've turned into quite the lady killer."

"What?! Where'd you hear that?"

"From the same source who told me that you're packing serious heat. And she was certainly right about that. Mmmm!" She ran her fingers lavishly up and down his shaft, making sure that he knew exactly what she was referring to.

Her increasingly aggressive and effective stroking style worried him. Oh man, I'm gonna die! We're gonna crash into a tree with Heather jacking me off! At least now we're off the busy streets. If a cop saw me, he'd arrest me for reckless driving for sure; I'm all over the road!

He looked down at her sliding hand and said, "Um, can you kinda take it easy there?"

Instead, Heather stroked him at an even faster pace. "This same little bird told me that you've got incredible stamina. If that's true, this should be no problem for you, right?"

Although he knew he was being stupid, he couldn't help but take that bait - he had to prove to her that the things she'd heard about his sexual prowess were true. He grimaced and kept working his PC muscle in a determined effort to delay his climax. I can do it! Aunt Suzy's training. Actor in a play! Nerd power! I can't let Heather get the best of me!

That helped just enough so he didn't feel like he was about to spurt his load at any second.

With that crisis passing, some part of his mind wondered who this "little bird" was. Then he remembered that she'd mentioned Kim's name earlier. Dammit! Damn you, Kim! But then again, I'm not exactly suffering here. And I'm the one to blame, since I didn't think to warn her to keep quiet. I just assumed that went without saying.

When he arrived at Heather's house, after he managed to park safely, he finally let out a huge sigh of relief. We made it! Nobody killed! No car damage! Good God, never again. Never. My heart can't take it!

But now that the danger of an accident had passed, Heather started stroking him even more intently. She used both hands and upped the ante even more, pulling his balls out of his shorts so she could fondle them as well. She was having fun tormenting him sexually while testing Kim's claim about his stamina.

"What's the matter?" she teased. "Cat got your tongue? Something on your mind, perhaps? Something ... distracting you?" She laughed at his discomfort.

"God, stop! Please! I can't take it!"

"What? Are you having second thoughts about fucking me? Don't wanna fuck the head cheerleader?" Her hands flew up and down his shaft as she milked him for all she was worth.

"Arrgh!" He closed his eyes tightly and struggled mightily not to cum. His whole body tensed up as he struggled. He knew he couldn't last for long.

Suddenly, Heather laughed, stopped her stroking and removed her hands. "Well, I'll be damned. Score another point for Kim. She said you had the most amazing control, and you do. How is it you haven't cum already? If you were my boyfriend Rock you would have lost it about the first minute I touched you back in the Baskin-Robbins."

Alan groaned again at being reminded that the girl he was with was cheating on the hulky, dangerous quarterback. He was in no condition to explain his self-control techniques, because he was still clenching tightly, doing all he could not to cum. Even though Heather had stopped touching him, it was all he could do not to lose control. He felt like he was on the verge of hyperventilating and had to fight just to breathe.

He could sense a kind of cruelty in her, and he knew he'd just been very lucky. If she'd stroked him only a little bit longer, he would have lost it for sure and made a mess cumming in the car. He probably would have had to block his cum with his hands, leaving her laughing at him. Instead, he had impressed her immensely.

Heather abruptly opened the door on her side of the car and started to get out. "Come on! Are you just going to sit there? We have some hard-core fucking to do! Let's go!"

Even though he was aware that having sex with Heather was not prudent, he was a horny eighteen-year-old boy whose dick was doing all the thinking. His desire to fuck was so great that he couldn't restrain himself. He zipped up, got out of the car, and managed to make his way to her front door. He wanted to run into her house, but even though she pulled him along to hurry him up, his 'run' was more of a waddle - he moved like someone who'd just been kicked in the nuts.

He worried briefly that some of Heather's family might be home, since it seemed that she loved to live dangerously. Mercifully, he was relieved to find that the house really had been empty.

Heather pulled Alan up the stairs by his hand and they burst into her room. She immediately started removing her clothes. He saw that her blue jeans were so tight that it was quite a wiggly struggle for her to get them off.

Alan was happy for the delay. Not only was it a sexy sight to watch her remove her jeans, especially since she'd pulled her top up to her shoulders first, but it gave him a minute or two to calm down after the whirlwind of events that had led him here. The sight of her big, well-tanned breasts bouncing around didn't exactly cool his ardor, but the lack of any direct tactile stimulation provided some immediate relief for his dick.

As Heather continued to somehow peel herself out of her blue jeans, he noted with surprise that she had no panties to take off, which meant that she must have gone without any for the whole afternoon at the very least. That observation made it even harder for him to calm down.

He decided it would be better to look elsewhere to reduce the visual (and mental) stimulation, if he was going to have any hope of living up to Kim's hype. He looked around and was surprised to see how girly and frilly Heather's room was. He guessed that she hadn't changed it much since she was a lot younger.

He thought, Okay, a chance to take a breather. Let's review. This is a pretty scary situation. Somehow, I feel that Heather is just like a shark: if I show any sign of fear or weakness, she'll eat me alive. But why should I be afraid? I'm not the nerdy, virginal kid she thinks I am. I'm having sexy fun with Mom, Aunt Suzy, Sis, Glory, Kim, AND Akami! And now it looks like something with friggin' Brenda could happen!

In fact, speaking of Brenda, I need to remember the training Aunt Suzy was giving me last night. She said that instead of acting like it would be an honor for me to be with Brenda, I've gotta act like it would be an honor for Brenda to be with me! The same goes for Heather. I've gotta take the upper hand and never let go. No fawning! Cocky and confident instead. Play hard to get and make her want to try to impress me.

Man, I can totally do this. Compared to some of my other lovers, Heather isn't so great. Oh yeah, and role-play. I'm just an actor in a play!

Heather could tell that he was so busy thinking that he was ignoring her, and she didn't like being ignored. So even though she'd just taken her top off, she put it on again, but kept it rolled up to just under her armpits. This allowed for a whole lot of bouncy breast action that she figured was sure to catch his eye.

She was right. His strategic thinking melted away and he stared with infantile glee. He really was a tit man through and through, but the rest of her body was just as impressive.

She was well aware that if a guy had already cum once, he generally lasted much longer the second or third time. She also knew that Alan had suffered greatly from all the teasing in the store and the car and was now liable to shoot very quickly. So she had him sit on her bed, then knelt in front of him, pulled his pants and boxer shorts down, and resumed jacking him off.

As she started to stroke him, she said in a sultry voice, "So, did you ever think you'd be in my room with my hand around your cock, about to fuck the mighty Heather Morgan? Have you dreamed of fucking me? Have you masturbated just dreaming about it?"

He was about to answer each of her questions honestly. He had in fact masturbated many times while thinking about her. He found it a bit odd that she called herself "the mighty Heather Morgan". Then at the last moment he remembered how she mocked guys at the beach who were too worshipful and fawning, and that reminded him of his strategic thoughts.

After all the excitement in the car ride, he knew that he was right on the verge of cumming and no amount of fighting it would delay things for long. So he closed his eyes and simply ignored her question. He figured she'd see his "just about to cum" face and excuse him for not answering.

Sure enough, less than a minute after Heather resumed stroking him, he felt his balls tighten, causing him to yell "Cumming!"

Heather got off at seeing just how far she could get her male lovers to shoot, and to see who could shoot the farthest. So she held his shaft at a forty-five degree angle to maximize the trajectory of his spurting.

They both watched his cum fly high into the air, sailing in a great arc and landing on the carpet about four feet away.

He thought to himself that she'd regret wasting it like that if she only knew how good it tasted, but he was too insecure to tell her that. Instead, he fell back on the bed in emotional and physical disarray.

In contrast, Heather was hopping about with energy, unusually chirpy and happy. Kim's comments about the poor quality of Heather's "caveman" lovers had been closer to the mark than Kim had realized. Thus Heather was unusually excited to try someone new and different.

As she waited through Alan's refractory period, until his penis could rebound, she went back to the questions that he had answered with only a vague "Uh huh." She was so vain that she wanted more adulation than just those few words. She prodded, "Alan, you were saying about how you've wanted me forever?"

Alan, though, remembered again how she'd treated him at the beach, and that she had no respect for guys who fawned over her too much. He also trusted his instinct and his recent training with Suzanne, both of which suggested that he should feign indifference. So he replied, cleverly yet fairly honestly, "Sure, you're beautiful. Very beautiful. But to be honest, you're not exactly my type. I've kind of always pined mostly for Christine."

He didn't realize it, but that was about the most effective thing he could have possibly said. Christine was Heather's second biggest rival (behind another girl named Donna), so that fired her competitive instincts.

Even though Simone had recently told her about Alan's crush on Christine, she pretended not to know about it so she could vent her frustration. "Christine? You're joking, right? What do you see in her? Sure, she may have boobs. Okay, very big boobs. And I'll admit she's got a nice face and probably a halfway decent bod, what with all the sports she does. But her personality! Gaawwwd! Give me a break! Is she trying to win the 'Miss Goody Two Shoes' award or something? She makes me gag. Jesus! What a prude. And what a demanding bitch, too! She's so high maintenance. A virgin bitch. What a sorry combination. Whatever do you see in her?"

He thought that that wasn't the moment to point out that Heather was the pot calling the kettle black when it came to bitchiness. He figured he was pushing his luck already by not praising Heather to high heaven, so he answered half-jokingly, "I guess it must be the boobs."