6 Times a Day



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William Osborne

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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.

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.