6 Times a Day

It turned out that Alan didn’t have much time to recover, because he had to get ready for his “non-romantic” date with Christine. They already had plans to have dinner and see a movie.

As he left to pick up Christine, he thought about her. You know, it’s ironic. Before she shot me down, we were friends, but just school friends. We never did anything outside of school together, like, at all. And now that she’s rejected me, we’re basically going on a date to patch up our friendship, the very kind of date she shot me down over! But the key difference, sadly, is that it’s understood that this is a completely platonic date.

Alan picked up Christine at her house, and was surprised to see that she was dressed as if she were going on a real date. He had dressed somewhat nicely, wearing a collared shirt and slacks for a rare change from his usual T-shirt and shorts, but she had really outdone herself. He’d dreamt about seeing her cleavage countless times, but he never had, not even when she was wearing various sports clothing. She was very scrupulous about wearing high necklines, which only added to her mystique with the boys. But now he could see her tantalizingly deep valley in nearly all its glory.

His dick immediately got hard, extremely hard. Although he was resigned not to pursue her romantically, he still got intensely aroused almost every time he saw her.

As he came up to her, he said, “My gosh, Christine, you look absolutely fantastic!”

But then realizing this wasn’t supposed to be a “real” date, he joked, “In a completely platonic sort of way, of course.”

She laughed at that. “Thanks. Do you really think so?”

He joked, “I try to, but you make it hard whenever I’m around you.”

He belatedly realized the double meaning in his words and thought to himself, And I definitely do mean that in more ways than one!

She laughed again, but a little nervously this time, because she caught both meanings. Still, she was insecure about her looks, remarkably enough, so she eagerly ate up his compliments.

He piled it on. “I’m serious. You look so … womanly. So mature. I’ve never seen you in a skirt – it turns out you have legs! I was pretty certain you had feet, but beyond that I wasn’t so sure.”

She laughed some more. “Do I dress that badly? Maybe I need to wear shorts and skirts a little more often.”

“Please do. Don’t hide your legs because… What legs they are! And you’ve got a purse, like a lovely lady. Lipstick, even! And is that rouge on your cheeks? Wow! I’m honored to be with such an enchanting creature. But with you no makeup is necessary because it’s impossible to improve on perfection.” He wanted to compliment her cleavage as well, but he didn’t know how to do that without sounding like a letch.

She was smiling broadly now. “Stop that … eventually! I’ll give you two hours to stop the flattery. Seriously, you know I really meant it the other day when I said I’m not ready to go out with anybody. Right now I can’t let anything distract me from getting into the college of my choice.”

“You know you’re already a shoo-in anywhere in the country.” He was certain about that.

“Don’t be so sure. This semester will be the most crucial. I figure this is probably going to be the closest thing to a real date for me in a long time, so I wanted to go all out. I hope you’re not weirded out or getting the wrong idea or anything?”

“Absolutely not. I’m just platonically delighted to be spending a lovely evening with a very lovely lady. Emphasis on platonic.” He looked jovial and gave her a friendly wink.

With over-the-top theatricality, he made a sweeping bow and then held out his hand. “Come, my lady. A big fat evening of fun awaits.” He was making a joking reference to the fact that they had plans to see the movie “My Big Fat Greek Wedding,” and then have a late dinner afterwards.

He thought, Man, I just hope she doesn’t notice “My Big Fat American Penis!” These slacks aren’t good for hiding my raging boner, and she’d probably get offended. But what does she expect, when she looks that great?!

She took his hand and stepped towards his car.

But to her surprise, he kissed her hand before walking her to his car, arm in arm.

Although his gesture was unexpected, she wasn’t concerned. It was obviously just a fun kiss, not an “I’m trying to get in your pants” kind of kiss.

He said, “To be honest, I haven’t exactly been on a lot of dates myself, and my prospects don’t look so hot. So I figure this can be a kind of fun practice date for each of us. Don’t mind me if I ham it up.”

“Mind? I think it’s great. And I love the ‘practice date’ idea. That’s a good name for it.”

Just as he was about to start the car engine, he said matter-of-factly, “By the way, this is a car. More specifically, it’s my family’s minivan. A car is something that takes us places quickly.”

She looked at him like he had two heads. “What the hell are you talking about?!”

“Oh. Well, I figured that since you’re blonde, I need to explain the basics. But I’m probably using big words that you don’t understand. Let me try again: This. Is. A. Car.”

She reached over and hit him on the head, but she was secretly amused. She didn’t find his Dumb Blonde jokes sexist, because she knew he wasn’t like that, and in fact he only used those jokes on her. It was more of an ironic commentary on the fact that she was, by far, the smartest person he knew.

“Ow! That hurt!” He reacted like she’d seriously punched him, when in fact she’d hit him with the force of a typical slap. This was part of their routine: he’d tell a Dumb Blonde joke, she’d act offended and tap him lightly, and then he’d pretend to be mortally wounded. It was silly and predictable, but they both enjoyed it.

As they talked and joked, Christine thought, What’s gotten into Alan? This is great! He’s so much more confident than before. Is this the same guy who was slumped down and afraid to look me in the eye when he asked me out last month? I thought things might be weird, especially with the rather bold way I dressed, but he’s completely at ease, and that puts me at ease too. Could it be that he’s finally over me, and because of that he’s not all fumbling and nervous around me anymore? I hope so. I like this new Alan a lot more than the old one.

Little did Christine know, but there was a different reason for his greater confidence and more overt masculinity: all the fantastic sexual encounters he was having with the gorgeous women at home had pretty much obliterated his fear of being close to beautiful women.

In fact, as they got into his car he secretly marveled at how he could rub his sister’s dripping pussy with a brush one hour, then innocently chat with Christine an hour or two later. It all seemed so surreal, yet wonderful. He thought, To think: not long before this “practice date” started, Sis gave me not one but TWO handjobs! Kat, of all people! If Christine only knew, she’d literally kill me! Yet here I sit, cool as a cucumber. I’m getting really dang good at rolling with the punches, that’s for sure.

The “date” went well. Neither of them liked “My Big Fat Greek Wedding” much, finding it too lightweight and plotless. But afterwards at dinner, at a thematically-appropriate local Greek restaurant, they had a lot of fun analyzing it and tearing it apart.

There was no mention, no matter how oblique, of what had happened when Alan had tried to ask Christine out. There were no serious discussions about where they stood with each other. Instead, they just kept it light and had fun.

The only snag Alan had was that his penis stayed erect more often than not. True, the tantalizing glimpse of Christine’s cleavage was a big factor, but he figured he would have been aroused no matter what she wore, just because he was with her. When she finally loosened up, which could take a long time, she could be surprisingly charming and witty.

He was so happy being with her that he started to suspect he was still in love with her. He wondered how that was even possible with all the other exciting things happening to him lately, but there was no explaining love. Still, he didn’t let himself pursue that line of thinking, since he was trying hard just to have a good, non-romantic friendship.

When Alan dropped Christine off as the evening ended, he again was over the top with his chivalric gallantry. But it served as a good excuse for him to give her a good-night kiss on the cheek at her front door. .𝘤𝘰𝑚

As he drove home, he thought, That was a blast! But the whole thing is so ironic. The only reason I could be so witty and charming is because I now know there’s no romantic possibility between us. Otherwise, I would have been a nervous wreck. But as a result of my new attitude, we clicked so well that it started to seem like there WAS something romantic between us.

I mean, with that goodnight kiss I got the impression that Christine wouldn’t have minded terribly if I’d kissed her some more. She kissed me back, nearly on the mouth, and then almost looked sad when I pulled away. Or was that look just my imagination? I don’t know. Probably just wishful thinking on my part. I wish I had more experience with things like this!

In any case, it’s a moot point. It’s too late for us to be a couple because of all the crazy stuff that’s happening to me at home. She’d never allow that to continue if she knew – not that I could ever tell her! – and I love it too much to stop. All of a sudden, I’ve got more girls than I can handle, which is yet more irony. A few weeks ago, I felt like I’d be celibate and single forever. As much as I loved Christine, I love Sis a lot more. But still, maybe Christine and I can do this kind of thing more often and just have a nice time together, now that the romantic pressure is off.

So, before his memory of Christine faded, he jacked off another two times.

Christine also ruminated after Alan left, What has gotten into him? I could get used to fun evenings like this one. Before, he used to make me nervous with the way he’d be anxious around me and always stare at my body, but tonight he put me at ease and made me feel good about myself. Now, I just know I’m gonna be smiling for hours. I wish I would have known he could be like this before I turned him down.

Did I make a mistake?

/////////////////////////////

Please consider Donating however much you can to support me.

Every Little Donation motivates me to do better works.

—————————–

https://ko-fi.com/snake_empress

/////////////////////////////