6 Times a Day-Chapter 1057 Alan - It Seems Our Friendship Is Getting Deeper!

Current Patreon Members:

Silver Tier:

William Osborne

Broze Tier:

Danial Haxton, Tangents, JustGotHit, Killstroyer, VoidStar, WendigosArk, Jester Smash

---------------------------------------------

Alan thought, Just like Glory. If the two of them ever started an investigative agency, they'd be unstoppable. But actually, maybe I can turn this to my advantage. Why not be a little forthcoming about this for once? If she realizes just how many girls I'm sleeping with and who some of them are, maybe that'll make her realize that there's no way I could ever have her, and her alone, as my girlfriend.

So he said, "Nah, don't worry about it. I'm probably being too defensive. If you're so secretive about the stuff you tell me, then I can trust you with the stuff I tell you, right? Normally I have a very strict 'don't kiss and tell' policy, but I'm hoping that since you're becoming such a close platonic friend I can confide in you and not worry about getting backstabbed."

She looked up hopefully. "I'd like that too, very much. You can trust me completely. My lips are sealed."

"Okay... Well, the rumors are true. I have had sex with Heather."

"Heather." She spat out the head cheerleader's name as if it was a vile-tasting piece of food she'd been choking on.

Heather had her share of enemies, but Alan was surprised by the level of reflexive hatred Christine displayed. What Alan didn't know was that Heather and Christine had a long-simmering rivalry that predated Alan's sexual awakening. Heather and Christine were known as the school's two reigning knockout blondes, and that fact alone had put them into competition with each other a couple of years earlier. Christine hadn't really cared at first, but Heather was so keen on "proving" that she was the best that eventually Christine had started fighting back.

Christine was very satisfied to finally confirm that Alan and Heather were sexually intimate, even though the fact itself disappointed her. But she didn't take any time to think about it further at that moment, because she wanted to push for more information while he was still in a revelatory mood. "Heather and...?" she prodded.

"Well, you probably can guess where Heather goes, Simone isn't too far behind. But you probably know that already since I understand Simone doesn't go out of her way to deny that she's been with me."

"Yeah, I already knew that. So, who else? What about the other cheerleaders?"

He found himself in a surprisingly proud, boastful mood. "Well, let's just say that if you're a cheerleader, the odds of your having had sex with me are pretty high. Except for my own sister, of course."

Just like the Heather news, Christine had been virtually certain of that already, so she wasn't very surprised. In fact, hearing that confirmed somehow even increased her already high arousal. She teased, "Hmmm. then I'll have to see how I can go about becoming a cheerleader."

He suddenly had a vision of Christine as a cheerleader. He could easily picture giving her painted-on panties and then fucking her in the theater room. Hold your horses, boy! Platonic! Keep things platonic, even if she's coming on to you like gangbusters. Don't forget what'll happen if she finds out about the incest. God, I think pretty much all the cheerleaders suspect I'm doing something with Sis. Just imagine if Christine talked to them about that!

That prospect cooled his ardor a bit. He was dreadfully afraid of her finding out about his incestuous secrets, since she would undoubtedly find a way to put a stop to something that she found so immoral.

She continued to pry. "So you're doing the entire cheerleader squad, even Heather. That's every guy's dream. God, you know, I can't help but be impressed by that, even though I know it's completely wrong. You're such a fucking bastard!" However, she said it in a playful way.

"I know. You're not the first person to tell me that."

She thought about what she'd just said and realized, It's true - that IS impressive! He's certainly having sex with Amy, Kim and Heather, and now he basically confirmed Janice and Joy too. That's not only impressive; it's downright arousing! Add Simone to the list, and I'm sure he could have had Donna if he wanted her. He's slept with literally all the other most beautiful girls in school! And now he's on a date with me, and he can have me too!

In actual fact, that wasn't true. Although Christine was extremely horny, she was far from ready for intercourse. When she thought about going wild with him, she was focused on just kissing and fondling, but the fantasy of him "taking" her in the same way that he'd taken all those other beautiful girls was like throwing gasoline onto her fire.

She propped her elbows on the table and rested her head in her hands. That caused her body to sway forward, putting her huge breasts on especially enticing display. If her red outfit hadn't been so skin-tight, her nipples probably would have been exposed to his gaze. She asked, "So how does something like that work, anyway? Don't some of them have serious boyfriends? And do they all know about all the others, and talk to each other about it?"

His eyes practically bugged out, thanks to her new pose. He furtively readjusted the position of his erection in his pants. But just that much touching of his throbbing hot boner caused him to lose self-control, so he reached into his pocket and found himself masturbating. Because his hand was inside his pocket and he didn't wear underwear anymore, all he had was one thin layer of fabric between his fingers and his shaft.

Dear God, she's gonna drive me crazy! I shouldn't be doing this. What if she finds out? But I can't help myself! Oh God! What if I cum in my pants, or make a big wet spot? This isn't good!

Despite distracting himself with his self-stimulation, he managed to reply, "Come on. Do I really have to answer that kind of stuff?"

Her eyes shone brightly. "YES!" She chuckled, realizing just how overeager she was. "Okay, sorry. Never mind that. So who else is there?"

"Well, some other girls here and there. Some of them don't go to our school and you wouldn't know them." That was an intentional misdirection, since she did know some of them like Katherine and Glory, but it was true for others like Brenda and Xania.

He continued more truthfully, even as he subtly continued rubbing his sweet spot through his pants pocket, "But there is sex as an expression of love, and sex as an expression of pure lust. I'm so lucky that Amy allows me to have fun playing around, but Amy is the one that I truly love. That's what matters." In fact, Alan loved Susan, Suzanne and Katherine at least as much as Amy, but he could never tell Christine that.

"I... see..." she said very slowly. Then, after a long pause, she blurted out so quickly that it was nearly incomprehensible, "Andwhataboutsexasanexpressionoffriendship?"

He just blinked. "Huh?"

She blushed, then lowered her voice, saying, "And what about sex as an expression of friendship?"

He understood that but was still momentarily thrown. "What do you mean?"

She blushed some more, her cheeks turning cherry red. In her mind, she imagined Alan standing naked at the doorway of a room full of cheerleaders. Heather was naked on her knees in front of him, giving him a blowjob. Amy stood naked to the side, holding a clipboard. She looked at Christine, who was standing in front of them all, and said to her, "So, Christine, let's see. Alan's put you on his approved-to-be-fucked list, so let's see if he can squeeze you in. Or, should I say, can all of him be squeezed into you, hee-hee? I crack myself up. Sorry... Hmmm. What a busy schedule. Maybe tomorrow afternoon between three and four? Would that work for you?"

To Christine's surprise, in the daydream she said, "Yes!" with great eagerness. 𝙗𝙚𝙙𝒏𝙤𝙫𝒆𝙡.𝒄𝙤𝒎

Amy replied, "M'kay! Super! Now why don't you help Heather and me with his blowjob. Alan likes a lot of tongues."

To Christine's further surprise, she found herself dropping to her knees and crawling forward.

Suddenly Christine snapped back to reality. God dammit! I'm too horny to think! I need to cool it, and fast! She responded, "Oh, nothing. Just a lame attempt at a joke. I guess I still don't have this flirting thing completely figured out."

She was torn. She'd always dreamt of a "Mr. Right," a knight in shining armor, perfect in nearly every way. Her new fantasies based around Alan's sexual prowess were disturbingly out of line with all of her dreams and longings up until recently, and she didn't like it. Yet she lusted after him so strongly that she was almost able to ask him if she could be nothing more than one of his "helpers." Almost, but not quite.

Meanwhile, he heard the "sex as an expression of friendship" comment and drifted off into fantasizing too, helped by the fact that he was covertly stimulating his sweet spot. He was particularly struck by the fact that she was wearing long arm coverings that left her hands uncovered but went almost up to her shoulders. That one simple accessory made her appear much more formally dressed, as if she were going to a ball, but also much sexier, especially given the way she normally dressed, fashionably but also very restrained.

The way the arm coverings and her top shone in the light brought up images of her as a go-go dancer. In his fantasy, she slowly stripped in front of a crowd until finally she wore nothing but her latex arm coverings and her even longer latex stockings. In real life, he doubted she knew how to dance at all, since she'd never been to any of the school dances, but in the dream she danced gracefully yet also with a wild abandon.

He suddenly became painfully aware of just how hard and stimulated his hard-on was. He sensed that if he didn't do something quickly, he'd cum, or at least leak an embarrassing amount of pre-cum. That realization brought him back to reality, so he stopped rubbing his sweet spot (although he continued to grip his erection). He guiltily looked at her to see if she could detect his arousal.

However, she still seemed a bit spaced out. With her daydream still on her mind, she attempted to change the subject by asking, "So is it true about the theater room? Is something going on in there? And what about Ms. Rhymer? What about the rumors of you and her being an item?"

He thought, Oh shit! She knows or suspects about all that too?! This is not good. I can tell she doesn't trust me fully, but why should I trust her? It would be nice if I could really have her as my confidant, but there are so many things about me she can never know. I can't let her know about Glory, much less my incestuous family. But I do need to throw her a bone.

So he tried to calm his concern by lying, "I can see how the Glory rumors got started. She is beautiful, and I do work with her as her teacher's aide sometimes. But that's all there is to it. She's a very responsible teacher and I'm sure she'd laugh at those rumors. As for the theater room..."

"Yeah?"

"Wait. First tell me what you heard."

"I haven't heard anything, to be honest. Except for a rumor that the cheerleaders go in there during lunch to smoke pot. But I've seen you headed in that direction more than once, and I know you don't smoke pot. You remember that discussion we had after that ridiculous anti-drug rally?"

"Yeah. Well, you're pretty sharp. I still don't do drugs, but I do take part in some other activities in that room from time to time."

"I see." Christine's daydream immediately returned, but the situation was slightly changed. She'd seen Kim, Joy, Janice, and Simone headed to the theater room at various times, so suddenly they were all there in the room as well. In other respects, her daydream resumed where it had left off. She crawled forward to try to wrestle some of Alan's boner away from Heather (who naturally would attempt to hog it in the dream, just as she would in real life). As she did that, she was able to look further into the room and saw the other girls sprawled all over the floor, panting with exhaustion and drenched in cum. Whether she realized it or not, her fantasy wasn't that far from the kind of thing that really took place in Alan's life on a regular basis.

However, she caught herself visualizing such images and thought, What is with me lately? Why do I always have such submissive fantasies? It's especially ironic tonight given that I'm wearing what could practically be a dominatrix outfit.

She began thinking along different lines, imagining herself as a dominatrix lording it over Alan. Wearing a stripped-down version of what she currently had on (which in fact exactly matched what she was wearing in Alan's fantasy), she fantasized about sitting on his face. She commanded him to lick her pussy, which he did with gusto.

She found herself greatly enjoying that daydream, even though she had no real conception of what being orally pleasured was like. As she started to come out of it, she thought, Now that's more like it! That would be awesome. Why can't my dreams be more like that? Actually what would be even better than submission OR domination would be to simply make love with him as equals. Will that ever happen? Why have all my dreams become so perverted lately?

Alan was once again looking down into Christine's ample cleavage, admiring the way it was lightly rising and falling with her breathing. He loved how she was still leaning forward on her elbows. He also couldn't help but notice her erect nipples, thinking they looked really sexy.

He was too busy with that sight to notice that Christine was a bit spaced out. Instead, he asked, "I gotta know: how it is you know so much stuff? I mean, I always look around when I'm headed to the theater room, and I could swear I've never seen you in that area."

She paused, once again considering what she could tell him. She decided that he was pretty observant too, and now that she'd revealed that much he would begin to figure things out, so it was best if she came clean. "You probably didn't. I've been down there a bit, but the fact is, I rely on some of my friends. We have a bit of a clique, and we help each other out."

"Aaaaah," he said, pretending as if he understood when in fact he didn't. In his previous existence as one of the school nerds he hadn't paid much attention to school gossip or politics, and now that sex was such a big part of his life he didn't have the time to spend with other students to learn the latest scoop.

She was a good judge of emotions. She smiled with amusement at his attempt to appear clued in, then explained, "The other girls sometimes call us the 'Goody-goodies,' although I find that name insulting. Girl stuff in school is like a whooole different thing than guy stuff. With girls, you're judged by how 'easy' you are. There's a bunch of us who kind of stand apart because of that. Many of us are still virgins, if you can believe that. So we sort of stick together. And I work with them as a kind of network to learn stuff. So you may not have been seen by me, but if you're seen by one of them it's almost the same."

"Ah. Now I DO see. Thanks."

"But wait! You have to PROMISE not to tell anyone about that, okay? If they knew I told you that, they'd probably kill me. In fact, I've probably said too much. In fact, I KNOW I have. Damn." She looked around furtively, as if someone could be listening.

He had to suppress a laugh. I know she means the "probably kill me" metaphorically, but that is still so funny. It's like we're Cold War spies or something. It's only some minor school stuff, but we make it out to be so life-and-death. Then he recalled being punched in the face, and being pushed down the stairs, so he amended his thoughts. Okay, so it's not totally minor. I need to pay a LOT more attention to what's going on.

"Christine, thanks a ton for telling me that much. I promise I won't tell a soul. I can see why you were so careful about secrecy with this meeting. If I tell someone, say, what you told me, that Jake isn't really in line with the other football players, that might get around and then Jake might realize, 'Hey, I told that to that goody-goody Serena. She must be the source of this rumor.' And then Serena will get in trouble, and maybe you'll get in trouble from her."

"Exactly. I knew you'd understand." She sighed with relief. She'd felt as if she were between a rock and a hard place, because there were some things she'd learned about Alan that she felt obliged to tell him, but by doing so she could be betraying the trust of her "Goody-goody" friends. If he could understand her difficult position, that would help.

"Wow," he said out loud as he mulled it all over. He even finally let go of the erection that he'd been stroking through his pants pocket. He put his hands back on the table, if only to prevent himself from losing control in that manner again. "So I've told you some secrets I shouldn't have and you've done the same for me. It makes me feel closer to you, like our friendship is getting deeper."

She was all smiles. "That's how I feel too."

For most of the rest of dinner, the two of them discussed strategy on how to defeat the football players once and for all. They pitched ideas back and forth to each other over generous helpings of red curry and fish cakes, and then mango sticky rice and fried ice cream for dessert. Their focus on practical problems and savoring their meals cooled them down so much that Alan's dick eventually became flaccid.

Almost everything they discussed was based on information from Christine's gossip network. Alan was very impressed with Christine's knowledge and the efforts she had gone to, and made her friends go through, to gain information that would help him.