6 Times a Day

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William Osborne

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As they waited for their check, their conversation began to wind down.

Alan said to her, “I must say… I can’t thank you enough. It’s almost like I’ve had a secret guardian angel these last couple of months. I mean, I can’t even begin to think how much worse off I’d be if you weren’t out there squelching rumors, sticking up for me, and who knows what else you’ve been doing to help that you’re still holding back from telling me about.”

She gave a knowing, secretive smile. “I can’t tell you everything all at once, can I? Keeping a few secrets lends me an air of mystery.”

“Yeah, we all have our secrets, I guess.” He was very mindful of his own incest and harem secrets as he said that. “But seriously, I owe you big time. How can I ever repay you?”

One thing immediately came to her mind, which involved Alan lying naked on top of her. To be honest, that was a big incentive for her continued secret assistance. But she’d tried to bring up the option of them sharing some casual intimacy earlier in the meal and had lost her nerve at the last second, as she usually did when that subject came up with him. She gathered up her great willpower and resolved to go through with it this time.

She blushed immediately, trying at first to bring it up indirectly, figuring she might have more success following through with that. “Well, you know how you and Amy have a special relationship…”

“Yeah?” He could already guess where that was going. He was both worried and delighted.

“I certainly wouldn’t want to intrude upon that in any way. I’d never want to take her, uh… But, um, she’s so understanding…” Suddenly, she blurted out, “Did you know that I’m still a virgin?” She immediately felt horrified that she’d said that; she looked like she was ready to crawl under the table in abject shame.

He had assumed that already. He knew it was a sensitive subject, but even so he couldn’t help but ask, “Christine, there’s absolutely nothing wrong with that. But I am curious, how is it, in this day and age, that a gorgeous, all-around amazing girl like you could still be a virgin? I mean, no offense.”

“None taken.”

He stammered on, “It’s just that… Again, no offense, but you’re so hot! You’d think that every horny guy for miles around would be after you. Eventually, someone would succeed.”

She modestly said, “Please. I’m not all that.”

He raised his hands in disbelief. “Come on! Believe me, you’re all that! And then some! And I’m not just talking about your famous boobs, or your equally impressive figure. Your face is just… devastatingly beautiful! And then when I think about the brains behind that face, that somehow makes you ten times more appealing. I don’t care what some guys say; smart is HOT!”

Her arousal had largely died away, but now it was coming back with a vengeance. “Enough with the compliments. Seriously. It makes me feel uncomfortable.”

“Sorry. Let’s go back to my rudely prying into your dating history.”

She laughed at that transition. She replied honestly, “Well, you know I’m not shy about telling annoying guys to get lost. I guess I come across as pretty intimidating, so very few have ever actually had the guts to ask me out. But I shot down even those few. The sad truth is, I have no dating history. Did you know that the only dates I’ve ever been on have been these non-romantic ones with you?”

“What?! You’ve got to be kidding! At the time I asked you out I was socially oblivious, but now I realize that there must be dozens of guys with serious crushes on you. Now that I’m more clued in to that kind of thing, I’ve noticed so many guys get all moony whenever you walk down the halls that it’s almost comical.”

“Yeah, but I don’t care about them. None of them are like you.”

He was floored. He thought, My God, she wants me. She really, really wants me! I should have said something earlier. I promised myself I would, but I’ve let things slide. I can see she’s working up to something. I need to put my foot down now.

He said, “Christine, we’re in a real bind. I’m really attracted to you and I’m pretty sure you’re really attracted to me. But as I told you on our last date, we can’t ever cross that line, because it wouldn’t be fair to Amy. As I’ve told you, she sees you as a threat to her relationship with me.”

Christine was stunned to hear him say it as directly as that. But she gathered herself together and replied, “Well, I know that. But I talked to Amy last week and kind of probed her feelings about this kind of thing. She didn’t want me to be another official girlfriend of yours, and besides that would probably never work; people at school would find that too strange. But she said that if you and I just wanted to fool around from time to time, she wouldn’t have a problem with that.”

Now it was Alan’s turn to be stunned. Shit! That completely undercuts my main argument! Curse Amy for being so completely cool and easy-going! What am I going to say now?! I can’t give her my real reasons: “Hey Christine, I can’t have sex with you just once because I know if I do it’ll be so good that I’ll want to do it again and again. And then before you know it, with you that much a part of my life, you’ll find out all about the incest. You’ll discover I actually have FOUR full-time girlfriends, and one is my mother and another is my sister! And then the whole thing will come crashing down around us, because everyone knows that when you don’t like something you don’t just sit around, you DO something about it. And not only that, but I’m so fucked out as it is that I just can’t give your undoubtedly wondrously tight, sweet pussy the regular fucking it undoubtedly so richly wants, needs, and deserves.” No, I don’t think I could exactly say that. So what DO I say? Shit!

Mostly to buy time, he asked, “But aren’t you completely morally opposed to that kind of arrangement? I thought you told Amy how grossly unfair and outrageous our arrangement is.”

She sighed. “Boy, you aren’t making this easy for me, are you? Yes, that’s all true. I don’t think it’s right that you can sleep around with anyone you want and she can’t. However… Alan, I have to be completely honest and lay all my cards on the table now that this has finally come out in the open. I’m a virgin, as I just told you. You’d guessed that already, right? It pains me so much to be one, now that my eyes have finally been opened to what I’m missing. I know I’m not an easy person to get along with at times, for a whole variety of reasons. I scare people away, to tell the truth. What I need is someone to be patient and gently guide me into sexual knowledge and intimacy and make me a real, complete woman. The problem is, I know it’s not going to happen anytime soon unless that someone is you. Hell, I don’t want it to be anyone else BUT you. I have such feelings for you, and well, uh…”

She couldn’t say more. It had been painful enough for her to say just that much.

He was torn. He took her hands in his while he thought. Finally, it was incredibly difficult to do, but he said, “That sounds wonderful. I’d love to be that guide so much. But I’m not the right person for you.”

He sighed heavily, while continuing to hold her hands. “Christine? You know what I confessed earlier about being involved with all those girls? Think about it. I’m spread really thin. I’m into all kinds of sordid stuff. Orgies, for instance. You might even say I have a harem of sorts. I mean, not exactly, but kind of, depending on how you look at it. I’m in really deep, in a very sexual world.”

She frowned. She wanted to be deflowered, but things like orgies and harems were a completely different matter. In reality, she didn’t want to have anything to do with crazy stuff like that, no matter what she might fantasize about.

“Trust me, Christine; you don’t want to get involved with me. I know you. Or at least I’d like to think I do. I’ve admired you for a long time now, and I picture you as the epitome of purity and goodness. You’re a one-man kind of girl. You’re a dreamer. You’re really extraordinary. You need and deserve a guy who can live up to your dreams and your high expectations. I’m not that kind of guy; I know that now. Back when I asked you out, you didn’t desire me then. And you still don’t, not in the right way. You’re just attracted because of this new ‘hot stuff’ reputation I have. You don’t need a scoundrel like me who can’t keep his penis in his pants for five minutes. You need a guy who’s as good and pure as you are. You need a better man than me to love you for your first time.”

She replied with surprising passion, “You’re wrong, Alan! I DID want you then. It’s just that… I was too shy to act on my feelings.”

She didn’t want to reveal the complete truth, which was that more than just her shyness had held her back. Even though there were many boys with crushes on her, she’d felt that Alan was very special in his own way, rising above all the others in her eyes. But at that point she’d been very high on the school social ladder, despite her goody-goody reputation and generally acting like she didn’t care about such things, and he was way below her socially, with a geeky reputation to boot. Her reputation at school would have taken a big hit if she’d gone out with him. Now, remarkably, he had become the most desirable catch of all. She didn’t want him to know the petty reasons that might have made the difference between her turning him down back then or her agreeing to his request.

He suggested, “Let’s forget what happened back then. That’s ancient history now, because I’ve changed so much since then. You have NO IDEA just what a wild sex life I have nowadays. If you did, you’d run screaming from me as fast as your feet could carry you. To give you one example, do you think you could stomach being in an orgy with Heather? Can you imagine sharing a blowjob with her?”

She blanched at that. Indeed, that prospect was really difficult for her to stomach. But there was a part of her, a naughty and sexually curious part, that actually found the idea appealing. Her mind flashed back to her earlier fantasy when Amy had told her, “Now, why don’t you help Heather and me with a blowjob. Alan likes a lot of tongues,” and she’d gone ahead to take part in a three-way blowjob with Amy and Heather. True, it had been just a fantasy, but it was still curiously arousing.

She found herself rubbing her thighs together with excitement. She was glad the table blocked him from seeing what she was doing. She was particularly aroused by the idea of Alan forcing her to take part in sexual acts with others like Heather. Her rational brain was appalled that she was finding such thoughts arousing, but she couldn’t help it.

However, she remained calm on the surface, seemingly ignoring his comments about his wild sex life. Instead, she said “I made a mistake, and I really, really do regret it. Moving forward, since Amy doesn’t mind-”

He butted in. “Look, let me tell you something about me that I’m just learning myself. There are guys who are happy to just have one night stands. They like to fuck and run, pardon my blunt language. Admittedly, there are a couple of girls I’ve done that with, girls who didn’t impress me that much. But the problem is, I’ve discovered that sex is a remarkable bonding mechanism. Most of the time, when I have sex with someone I find myself becoming emotionally involved with them. I want to have sex with them more and more, and that just increases the strength of the emotional bond even further.”

“And that’s a bad thing?” she exclaimed, growing more horny as she thought about having sex with him regularly. “It sounds wonderful to me.”

“Yes it is bad. Very bad. Because I know there’s no way that you and I could have sex just once. I’d enjoy it too much and you’d enjoy it too much. And then we’d want to do it again. And again. And again and again and again! But the really big problem is that you’re so all-around wonderful. So smart, so talented, so beautiful. Once I start down that path, you’re gonna become a big part of my life.”

She butted in, “What if I was really bad in bed? I promise to be bad. Let me be bad and completely uninteresting to talk to so we can have a mindless one night stand.”

He just rolled his eyes. “Nice try, but you know that’s not possible. You are who you are. I could see myself becoming extremely attracted to and involved with you. And that’s not fair to Amy. And it’s not just Amy either. I’m way overextended. If you were to get involved with me, in that way, you’d just be one of many, and there would be others I’m going to be much closer to, which wouldn’t be fair to you either.”

He went on, “You deserve more than that. Much more. You’re destined for great things. I know it. It would pain me not to be with you every day, and I’d feel like I’m stealing time from Amy when I was with you, and so on. And the closer we got, the more you would hurt too, because, what, between my homework and all the girls in my life, I couldn’t do the normal things boyfriends should do. Believe you me, my body screams yes but my rational mind says no. I can’t just follow my lust, regardless of the consequences. I’m practically failing out of school as it is!”

“But-”

“Christine, you need someone special, someone who can devote his entire heart and soul to just you. Isn’t that what you’ve always wanted? Isn’t that why you’re still a virgin, because you’ve been saving yourself for that one special person?”

“Yes, but…” She wanted to say that he was that special person, but she stopped herself. “Alan! I’m really surprised. And hurt. But you have a point. I’ll think about what you’ve said. I do want just one man.” Her thoughts again returned to her fantasy of waiting to be assigned a fuck time in Alan’s busy schedule, and she gave thanks that he couldn’t see into her imagination. However, his words calmed her down enough that she stopped rubbing her thighs together as if she were trying to rub kindling to start a fire.

She suddenly looked at him with alarm. “I hope you don’t think I’ve been helping you out all this time because I was expecting…” She blushed still more. Then she waved her hands in the air in frantic ‘No’ gestures. “It’s not like that at all! I’m gonna keep helping you, no matter what. I just see you as kind of a ‘babe in the woods’ when it comes to school politics. And you are a friend, even though things have been a bit weird and sexually charged between us lately.”

“That’s my fault, Christine. That’s because my crush got in the way of what should have been just a normal friendship. But now I really want just to be good friends with you. I need a female friend who’s just a friend, if you know what I mean. I really like you, and that’s why I think you deserve so much more than what I can provide. I so very much wish I could be your special guy. If you’d said ‘Yes’ two months ago, that would have been different. But so much has changed since then. To be honest, I’m not proud of how I’m running wild sexually, but I know myself, and I know that I just can’t stop. That part of me is here to stay.”

“I understand,” she said rather glumly. There was much more she wanted to say, but she couldn’t. She wanted to say, “Alan, I love you. I don’t care if you only see me once a week; it would still be so much better than never. Can’t you see I’m so lonely and hungry for love? I’ll be one of your helpers or whatever you want from me. Just love me!” But she realized that he’d made up his mind and she needed to leave with at least part of her pride intact.

She also wanted to say, “You may feel that you want to be just friends now, but don’t close the door. Maybe you’ll feel different in two months. Look how much things have changed over the last two months. Or even longer. I can wait!”

But she didn’t say that either. The truth was, she was already deeply in love with Alan, but she couldn’t tell him those things in the face of his rejection. She realized that he was right, in the sense that the very depth of their feelings for each other meant there was no way they could have sex just one time or a couple of times like two jaded, uncaring strangers. If they had sex even once, it was bound to lead to more.

Still, like people in love do, she held out hope in her heart that he’d change his mind, despite everything he’d said, or that their situation would change somehow. She wanted to help him with his school problems even more than before, to show him just how much she cared for him. She resolved to stay as close to him as she could so she’d be ready to take their relationship to the next level when an opportunity occurred.

With that in mind, she said, “Okay, I’ll think about that. I’m not saying I’m just gonna totally give up on the idea, because I can’t. The heart has a certain momentum, and right now all I can think about is you. But despite all these feelings hanging in the air, can we please keep having these dates? Non-romantic or not, I’ve enjoyed them so very much. I love dressing up and being treated like a lady. And the flirting practice and everything too. Please tell me we don’t have to stop.”

Against his better judgment, he said, “Sure, I’d love that. Over time, with these dates, maybe we’ll both get used to the idea that things really do have to remain platonic.” 𝙚𝙙𝙤𝒗𝒆𝒍．𝒄𝙤𝙢

However, even as he said that, he knew it wasn’t likely. If their past dates were anything to judge by, such encounters would only further inflame their lust. On a subconscious level, he hoped that something would happen on one of their dates that would cause them to cross the line into physical intimacy. For instance, they could both get drunk and then there would be no telling what might happen. Like her, he wanted to find a way to get things started without having to take responsibility for his actions. That way he wouldn’t have to feel bad about not living up to his own moral standards, let alone hers.

Christine was simply too desirable. Not only was her body out of this world, but he really liked her personality. He even liked her “flaws,” such as her stubbornness and self-righteousness. Deep down, he knew that he just had to have her someway, somehow.

If only he could be assured that she wouldn’t destroy his entire family when she found out about the incest, he would have thrown caution to the wind and tried to figure out ways to overcome or at least manage all the other problems between them. But he knew her well and had observed her acting with dogged determination according to a strict moral code. He was certain there was no way she’d say, “Sure, have sex with your sister and your mom. Just make sure to save some of that big cock for me.” He was afraid to even mention the idea of incest to probe her opinion of it, for fear of tipping her off.

They sat drinking their after-dinner coffees for a while, with both of them feeling and acting awkward. She tried her best to smile, but it looked forced.

He felt conflicted but kept reminding himself that what he was doing was the right thing to do.

He thought, It’s insane. I have four women I’m completely in love with and committed to, and that’s not even counting Brenda or Glory. And God knows what the situation is with Heather. Or Simone! I could really get into her. I’ve promised myself that I have to cut down to just the ones I love the very most. I HAVE to do it! There’s only one of me and only 24 hours in the day.

I can sense trouble brewing with them, like the way Mom practically raped me a couple of hours ago, she was so needy. I just can’t spread myself any thinner, no matter how kind, beautiful, and frankly, big-busted Christine is. And what about jealousy? Sis in particular gets really steamed about Christine. Not only would that cause a new outburst of jealousy… Oh! Sis would be heartbroken. Even Amy would be upset. I’d just be asking for trouble.