6 Times a Day

Alan pondered the news about Ron while he drove to Christine’s house. It’s a good thing that Sis spoke up about how she wasn’t so broken up about it, or I’d feel like a cad. I’ve got this whole Oedipal issue that complicates matters. She doesn’t, but even she kind of admits that this revelation is good news from a certain perspective. The bitter truth is that I’d given up on thinking of him as my father long before all this sexual wildness began.

Now that the shock of finding out has worn off, it almost feels like the logical conclusion to a separation process that began about seven years earlier, at least. And he was the one who was pulling away from us the whole time, so why should I feel guilty! I didn’t steal Mom from him; he let her go. Heck, he’s left her twisting in the wind for years!

Hmmm. I never understood why he withdrew from the family, not just physically but emotionally too. Maybe that started around the time he got his secret long-term lover. Maybe he loved Mom to some degree, but when his new lover came along, he felt like anything he did with her or us kids was like cheating on his “true love.” Heck, he might even have a full family over there, for all we know! Not likely, but it’s possible anyway. Amazing. It’s like I never really knew him.

At least I’m grateful that I found out about this after I had anal sex with Heather today. What fortunate timing! Amy is right that I’ve had a kind of anti-gay bias, but I hope I’m getting better. I think a lot of that was because I thought of anal sex as unnatural and disgusting. But it turns out it’s friggin’ awesome! At least if I’m the one doing the fucking, that is. Although I have no interest in doing that with a man, I have a new perspective on it. With all the lesbian and bisexual activity I’ve been lucky to be a part of lately, my attitudes are changing fast.

But still, I’m very resentful about Ron. Like I said back there, the real issue I have with this is the deception. I’ve got a sinking feeling that their entire marriage was a sham. He’s probably known he was gay since he was a teen, and married Mom as cover for his business and family. What a rotten thing to do to her! But then again, if he hadn’t done that, then they never would have adopted Kat and me and I wouldn’t be in the incredibly lucky situation I’m in today.

Dang! I could go round and round with this forever. But right now I need to focus on Christine; I don’t want to be a space case the entire evening.

He picked up Christine in front of her house, just as he had done for their two previous dates. For such special events he was allowed to drive Ron’s Beemer, which normally just sat in the garage.

Christine seemed intent on outdoing her previous outfits. The outfit she’d worn on her last practice date had been borrowed from her aunt Kirsten. That had worked out so well that she’d visited Kirsten again, who lived about half an hour closer to the heart of Los Angeles, and borrowed yet more clothes. In fact, she’d spent hours talking with Kirsten about fashion, and they mutually decided upon just the right outfit for the occasion. Luckily, Kirsten was a stunning, busty beauty who owned her own fashion-related business despite being only 25-years old. They were close enough in size for Christine to fit into most of Kirsten’s clothes, and Kirsten was kind enough to loan her pretty much whatever she wanted. It really was an ideal situation, especially since it saved Christine from having to buy all her own outfits.

Christine had ended up borrowing a number of outfits, so she’d have something to wear not only for this date, but for future dates too. Each one was sexier than the last.

All of this had built up her anticipation of this event. She’d wanted something that looked stylish and high class yet would still force Alan to take notice of her body. She had finally decided upon a dramatic dark blue evening gown. It had only one shoulder strap and a high cut up one leg, exposing flesh practically up to her muscular ass. Furthermore, she had applied tasteful make-up and wore what were for her extremely high heels, over three inches.

Susan turned out to be right that Alan would put the news about Ron out of his mind for the duration of his date with Christine. In fact, he was completely blown away from the moment he laid eyes on her. He actually contemplated not getting out of the car to greet her because he was afraid that there would be no way to hide his suddenly raging erection. Realizing that would be rude, he was forced to walk around the car and open the door for her, but he wasn’t entirely successful in hiding his arousal.

“Wow. That’s all I can say. Wow.” His eyes were practically bugging out. “If people at school saw you dressed like that, well, I don’t know what. There would be a lot of mayhem and gnashing of teeth.”

Christine laughed with delight. “‘Mayhem and gnashing of teeth.’ I don’t know what that means exactly, but I like it. And you’re not looking too bad yourself, mister. With that outfit, you might get the role for the new James Bond movie.”

She thought about her outfit. This had damn well better work. On a rational level I know there will be other women at the restaurant showing as much skin or more than I am, but I can’t help but feel like a complete hussy dressed like this! I’m not even wearing a bra! If Alan doesn’t get the hint this time, what can I do? Go naked next time? Maybe this’ll be the night for a breakthrough between us!

As she was eyeing him she spied the large bulge threatening the fabric of his pants. Oooh! Looks like there’s a little fellow here saying ‘wow’ as well. Looks like Aunt Kirsten’s help is paying off. It’s kind of exciting to feel exposed and know that I made him get aroused like that.

She discreetly took a second glance and then started to feel her insecurities take hold again. Okay, maybe it’s not such a little fellow. I always have a plan carefully thought out in advance, but what’s my plan here? I feel myself getting aroused just looking at his ample, er, endowment, but what would I do with that if I actually succeed in seducing him?

They got in the car and made it to the restaurant. It was a fine French restaurant called the Petite Auberge.

He asked, “Maybe this is being nosy, but I’ve just gotta ask: how did you get a dress like that?! It’s… awesome! I wish I could put into words the perfect compliment to express just how beautiful you look right now, especially when you’re dressed in that.”

Her face reddened because she was so bashful about compliments like that. She looked away in embarrassment. “Thanks. But don’t thank me. You should really thank my Aunt Kirsten. Just like last time, this is actually one of hers.”

“Wow! Please, please give my compliments to your amazing aunt!”

Alan was extremely aroused. His entire body seemed to be constantly buzzing with energy. Christine definitely does do something to me. Just an hour ago I was lazing around the house with Amy, Sis, and Mom. All three of them were in various states of undress, doing their best to get me going, but nothing. Nada. Alan Junior was dead as a doornail, and that’s saying a lot since all three of them are like runway models, and they were dressed in fancy clothes to boot. But one look at Christine in that evening gown and – schwing!

Not only that, but I was so tired I could hardly drive over here, yet now my heart is pounding and I’m so jumpy that I feel like I just drank a whole pitcher of coffee. I’m all nervous ‘cos it seems like she must want something to happen. For her to dress like that, that’s a huuuuge signal. But what does she want from me exactly? She knows Amy is my girlfriend now.

As soon as they sat down, he launched into some comments designed to dissuade Christine from getting the wrong idea, but doing it in a subtle way. “Christine, this looks like it’s gonna be another great evening. You know what I like best about our dates?”

“What?”

“Well, aside from the fact that I get to eat in the nicest restaurant in town with the most beautiful woman in town” – he couldn’t resist giving her that compliment, especially since it was heartfelt – “I like how the pressure is off. That means no worries and nothing but fun. If this was a real date I’d be all nervous and tense. But when I’m with you I can be 100 percent certain that nothing romantic could even be seriously imagined, since we put all that behind us.”

“Yes,” Christine said tersely, secretly upset to hear that he was closing off any romantic options. She’d grown increasingly determined to win him, or at least be with him in some way, since he now had Amy. But she just played along. “Me too. I think I’d be even more nervous than you, at least since you’ve turned into such a Don Juan.”

“Who, me?”

She practically growled, “Don’t play coy with me. You know I’m a straight shooter. I’ve heard all the rumors and stories at school. I heard straight from your new girlfriend that she doesn’t mind when you sleep with other women. I have a hard time putting this new you together with the old Alan that I’m so fond of.”

Alan, still determined to make his non-romantic intentions clear, thought, This could be a chance to scare her from romantic aspirations for good. I’ll just play up the whole harem thing. If that doesn’t get her into a snit, nothing will. She may even go into one of her high horse lectures about the whole inequality and hypocrisy aspect, and not without reason since there is a lot of unfairness when you look at things objectively.

He said, “Yeah, well, it’s still the same old me, just doing some new stuff. I don’t know what happened; a whole lot of luck has a big part to do with it I’m sure, but somehow I’ve found all kinds of success with the opposite sex. I mean, having an amazing and beautiful girlfriend like Amy who doesn’t mind me being with other women and even encourages it? How often does that happen? Every day I keep pinching myself, thinking I’m going to wake up from a dream.”

“So it’s true then. All the rumors are true?”

“Well, I don’t know about that. I haven’t heard all the rumors, and some of them are pretty crazy, I’m sure. But I do have a pretty amazing sex life all of a sudden, I must admit.”

She was crushed, but she tried not to show it. Instead, she said in a semi-joking manner, “So the rumor we talked about that’s going around about you having sex in the teacher’s parking lot in the middle of class, completely naked, right there out in the open, on the hood of a car no less, with some other busty blonde, isn’t true?”

He chuckled, trying to laugh along with her. “Heh-heh. Yeah. I gotta admit, that was a pretty funny one.” Of course he’d really done that with Heather, but felt it would be unwise to admit to that fact. However, he did privately amuse himself imagining the array of shocked and angry expressions that would cross Christine’s face if he actually did tell her, since she hated Heather so much.

Christine was suddenly much more serious. She felt very uncomfortable talking about sex with anyone, much less Alan, but she forced herself to in order to clarify things. “So… who are you, uh, seeing, besides Amy?”

Alan was pleasantly surprised. “Is that all you’re going to ask? I thought for sure you’d rip me a new asshole about the shocking immorality of my new sex life.”

She laughed a touch too cheerfully before replying, “I would. It IS grossly unfair, for starters. But I promised Amy I wouldn’t give you a hard time about it. Besides, I love good gossip and I want to know the dirt more than I want to lecture.”

“I can’t kiss and tell. Sorry.”

Christine groaned in frustration. “Arrgh! You can do better than that. Come on. Give me a hint or two, at least.”

He thought carefully while fiddling with his cutlery, and then lied, “It’s true that I’ve been having sex with a number of beautiful girls. It’s kind of a mixed bag, though. The only girls interested in me when I already have a girlfriend are those who either have no self-respect or are big sluts, or both. You know the types.”

He’d lied because he hoped to put Christine in a bind so she wouldn’t be able to position herself as a prospective casual sex partner after he’d just knocked those kinds of women.

She cut in, “The Heathers of the world, in other words. She seems to fit the bill exactly. I’ve heard a lot of rumors about you and her. Any truth in those?”

He poked at his napkin for some time. But when he looked up he saw her trademark implacable intense stare and knew she wasn’t about to back down. He sighed, then nonetheless did his best to divert the conversation. “I’m really not at liberty to say one way or another about her or anyone else. But I know you’re in the know about what she’s really like, and that’s the kind of girl I’m talking about. You’re so much better than those types. To be honest, I really admire your standards and moral positions. For instance, the way you tore into Sheila to her face the other day about how she’s ruining her reputation.”

Sheila was one of their mutual classmates. Neither Alan nor Christine knew her very well, but that didn’t stop Christine from speaking her mind about her, in front of witnesses.

Christine responded aggressively. “Alan, I’m surprised at you. I thought you were a better person than to have double standards like that. Why is it that you apparently can sleep all over town but if a girl does it she’s a slut?”

“Hey, you were the one laying into Sheila.”

Christine seemed a bit flustered, but replied, “I wasn’t knocking that she has sex, because if she does, that’s her business. I was criticizing her for being so indiscreet about it. Unfortunately, society does have this double standard, where most guys can and do brag about all their conquests but if we girls don’t protect our reputations we get all kinds of grief. That’s another reason I warned Amy about your arrangement with her. She’s a nice girl with a reputation worth protecting.”

He held up a hand and said, “Wait. You said you’d promised to go easy on me about that. And you should know I’m not the type to brag; you’re the one who brought it up.”

She laughed. “I guess I can’t help myself sometimes. The truth is, I promised not to go overboard. But I still hold the right to speak my mind about what I see as a gross injustice.”

Despite her criticism, he thought, Huh. By Christine standards, she’s letting me off pretty easy. She’s even joking a little bit instead of attacking me with that laser-intense killer stare she has. I guess she’s not THAT upset about things, which is strange.

I wonder if she’d loosen up enough about it so I could eventually ask her if she was open to playing around a little bit? What would be so wrong with that? Come to think of it, why AM I so resistant to having sex with this complete knockout who’s super-intelligent to boot?

I have to remember that I’m holding back, not just for my sake but mainly for hers. God knows I’d love to jump her bones this very minute. Just staring at all that glorious sweater meat in front of me, straining against the fabric, practically begging to be set free from confinement – damn!

Calm down, boy. She’s too good to be treated like a fuck toy. It would be like getting a Rhodes scholar addicted to crack. It’s just wrong, and a waste. She is too fine and amazing a girl just to be one of my crowd. Okay, my harem, if I can really call it that. If she’s gonna be pining after me, then she won’t be able to open her heart for some real “Mr. Right” who might come along.

Not only that, but if she were to find out about everyone I’m having sex with, she’d probably call me some pretty choice names and then lop my head off altogether. That’s not even much of an exaggeration – she scares me sometimes! And some of us have loose lips, especially Mom who seems to be in some kind of sexual fog half the time these days and isn’t that aware of what she’s saying or doing.

Or what if Christine simply got close enough to feel like she could drop by my house unannounced? What a disaster that would be! All she would have to do is step inside and the overwhelming smell of pussy would probably give everything away, especially with her ability to piece bits of evidence together. And forget it if she starts talking to Mom! I could just see Mom making small talk: “I’m so proud of my Tiger. He’s such a well-hung, cum-filled boy. Has he tamed your pussy yet?” Ugh! 𝗼𝐯𝗹．𝐞𝘁

So if she gets too close to everyone then I’m ultimately doomed. I don’t know what Christine would really do if she found out, but the disparaging and disappointing looks she’d give me would be devastating. It would be as bad as Glory finding out. No, worse! I have to protect my harem above all else, even if it means missing out on things sometimes.

With new resolve, he increased his efforts to make clear once and for all that any kind of physical relationship between them was out of the question. “That’s true; there is an inequality. But you should know that I’m not completely free to play around with just anyone. I do consider Amy’s feelings, you know. I wouldn’t do anything to hurt her. To give you just one example, she would be upset if I got involved with you because obviously you wouldn’t be just a mindless fling, given the strong feelings I used to have for you in, you know, that way.”

She thought out loud. “So she’d see me as a threat. That I’d replace her as your girlfriend.”

“Something like that. Luckily, it’s a moot point since we don’t feel that way about each other. That’s why she trusts me to go on these practice dates with you. That’s also why I can feel completely at ease with you, because with you and you alone I could never do anything even if I wanted to, since I wouldn’t betray Amy or her trust in me.”

He thought to himself, That’s not exactly true, but it’s close enough for horseshoes. Amy did seem displeased at me for going on this date, despite her trying to put on a good face. If this is what it takes to firmly move my relationship with Christine into a safe zone, then so be it. I’ll just have to get the story straight with Amy later.

“I see,” Christine said while thinking intently. Curses! He’s really trying to slam the door shut. What am I supposed to do about that? I can’t betray Amy, since she’s such a nice girl, even if I had it in me to do something like that, which I don’t. Then there’s the promise to not interfere with their relationship that I made to her too. I have to live up to my own ethics, not to mention that I’m hopelessly at sea at this seduction thing. Damn. It just seems so right that Alan be the one to introduce me to intimacy and love. I’m so frustrated that it doesn’t seem like that can happen now.

But maybe there’s a loophole. What if I got Amy’s permission for him to have a second real girlfriend, and not just another ‘helper’? It would be a bitter pill for me to swallow, but if Amy agrees, how can he say no to that? Amy is pretty amenable and I can be clever. I’ll bet I can work out some kind of arrangement with her, once I get a chance to talk to her about it. That leaves me SOME hope.

In the meantime, I need to work on this whole flirting thing, just for the experience. Who knows, maybe I can get Alan to see me in more of a sexual light. But I don’t really have a clue about how to flirt, except by dressing scandalously. Maybe I can use that to my advantage, though…