6 Times a Day

Back at the restaurant, Alan and Christine turned to safer topics for a while. But some time later, Christine redirected their discussion back to flirting, hoping to use her inexperience as an excuse to practice flirting with Alan. During a lull in the conversation she said, “Since we’re so safely platonic with each other, I have a big favor to ask you.”

“What’s that?”

“Well, this is kind of embarrassing, but I won’t beat around the bush. I’m hopelessly out to sea when it comes to flirting. Can you teach me how to flirt?”

He was surprised. Christine and flirting? Those are two words that do NOT go together. But on the other hand I never would have imagined seeing her dress like this, so maybe anything is possible. He replied, “I dunno, the last date we were on you said some pretty flirty things. I was pleasantly surprised.”

She replied, “God, this is even more embarrassing. The truth is, I had some lines I’d thought out in advance. Even some things I said earlier tonight, like saying you could be the new James Bond, were already in my mind before you showed up. I knew you’d look sharp so I was thinking about what I could say. Isn’t that dumb? Ugh! But I don’t know how to be truly spontaneous. I just feel so awkward all the time. I’m hopeless!”

He fidgeted nervously. “Ah. Well, first of all, I’m no big expert. But I’ve learned a few things these last couple of months so I’d be glad to share what little I know. Having some thoughts already in your head is no sin, for one thing. To create a sexy, flirtatious situation, sometimes it helps to force the issue. Like maybe you have a good line in your head and you find a way to bring the conversation around so you can use it.”

“Can you give me an example?”

“Well, a great way to flirt is with word play. I’m sure you’ve seen it in the movies and whatnot. You’re so smart that I’m sure you’ll pick up on it in no time. For instance, pick some common expression or idiom. Go ahead and pick something.”

“Okay. Knock on wood.”

“That works. So you have to think: how can I make something sexual out of that? Since ‘wood’ is also slang for an erection, there are lots of possibilities. For instance, if you told me, ‘knock on wood,’ I might joke that I’m not going to let you tap on my crotch.” He paused, then added, “You can do a lot of things to my crotch, but I hope knocking or tapping on it isn’t one of your first choices.” He winked.

She blushed slightly as she thought about that suggestion. “Huh. I get the idea, and I’ve seen enough examples from others flirting, but the problem is I tend to overanalyze things and think too much. And I’m shy about this stuff. Sometimes I have a really naughty, funny thought in response to something, but I’d never share it, even with a close friend. It would ruin my reputation, for starters.”

He said, “Well, that’s what these practice dates are for, to try things out and not worry about reputations or consequences.”

He didn’t realize it, but there was one problem with him teaching her about flirting – he didn’t really understand it himself. In recent weeks, his life had turned so sexual that “subtle” wasn’t exactly in his sexual vocabulary. What he considered subtle flirting would be outrageous innuendo to almost everyone else.

Christine also was so inexperienced that she had no idea when a come-on would be seen as too overt. However, she was determined to do whatever it took to begin to overcome her Ice Queen reputation. Hopefully, in the process she could lay the groundwork to somehow snag Alan as her boyfriend someday.

“And that’s what this is for.” He lifted up the half-full glass of wine that sat at his place at the table. He’d used a fake ID to order some wine for himself, but hadn’t had any way to do that for his date. “Drink some more. It definitely loosens the tongue.”

She looked at him with worry. “What if we get caught?”

“You can just say you don’t have any ID on you. After all, I’ve looked at your dress very closely, and I didn’t see any pockets.” He winked.

She squirmed a bit in her seat, getting excited as she thought about him closely examining her body. She was acutely aware of the fact that she wasn’t wearing a bra, and she wondered how obvious her erect nipples looked to him.

He asked, “What’s the worst they could do? Throw us out? Come on, live a little.”

She thought about it, concluding, He’s right. I need to live a little. She leaned forward and said in a husky voice, “Alan, are you trying to get me drunk so you can have your way with me?”

His eyes went wide with genuine surprise and arousal. “Whoa! Sexy! See? That’s big-time flirting.”

She snickered happily. “You mean that got a rise out of you? Wait! That phrase has potential, getting a rise. I know I got a rise out of you, but did I really get a rise out of you, if you know what I mean? Stand up and show me the evidence!” She giggled.

However, a part of her was shocked at her own words. I can’t BELIEVE I just said that! What’s happening to me? I feel kind of slutty for saying that, but I like it!

He laughed. “Good. You’re such a smart person; you’ll be a natural once you put your head to it.”

“Perhaps. But I’d rather put YOUR head up to it, if you know what I mean.” She giggled again.

Her arousal was growing. Her thighs tingled as she rubbed them together. This is NOT me! Or is it? Why does just saying a few words make me so horny all of a sudden? They’re only words, right? It’s not like he’s really going to take his penis and actually put it… Oh God! Seeing the glass of wine he was offering to share placed in front of her, she picked it up and took a big sip.

He thought, Uh-oh. Instant boner. Her voice has turned so sexy there’s no doubt about THAT double meaning. Now all I can imagine is taking that gown off and lining my “head” up with her hot, juicy pussy. Shit! Now I can’t get that image out of my head. Actually, I wouldn’t mind putting my big head there either and smelling and tasting her down there, teasing her clit with my tongue until she cried out like a desperate, rutting animal. Oh man. Down, Alan Junior, down! This is not good.

He said to her, “Uh-oh. I think I’ve created a monster. I have a feeling you’re not just going to best me in flirting, I’m gonna get totally creamed.” .𝙘𝙤𝙢

Christine’s eyes lit up. “Oh! That’s an easy one. I’m hoping that before the night is over, I’m the one who’s going to get totally creamed. How’s that?” She added in a voice absolutely dripping with sex, “Alan, will you please cream me?”

He groaned inwardly again. “Good. Almost too good. You’re too arousing already.”

She clapped her hands together, causing her braless boobs to bobble around inside her dress. “Oh goody! Of course, I never would say anything like that in ‘real life.’ I doubt even Heather would be that bold with her words. But here, we can do whatever we want.”

He nodded. “True. But there is one real-life effect to all this practicing. My body seems to be practicing getting aroused.”

She grinned. “Ah. So you’re raising the ante, eh? Two can play at that game. I’ll bet you’re just saying that. Stand up so I can see the proof! I’ll show you mine if you show me yours.” She laughed some more and took another gulp of his wine.

She thought, I can’t believe I’m acting like this. It’s like I’m looking down at a different me. But I do feel at ease. Well, kind of. I feel so nervous at the same time, too. I think Alan is the only boy I could say things like this to. Actually, I know that’s the case. What is he doing to me? I’ve never been this horny in my life!

He laughed along, but thought, Definite uh-oh. If she gets into a flirting groove, this is going to be a very long evening. Long and hard. And painfully throbbing. She’s sexy enough when she just sits there acting like a pure intellectual but if she starts acting all sexy like Suzanne? The mind boggles. Ay-yi-yi!

Christine, though, couldn’t help but rub her thighs together some more. Is that what I think it is? I’m getting all squishy down there, and my panties are hardly helping. How gross. But if feels so good to rub it, and he can’t see what I’m doing…