6 Times a Day

Iveyflame Special [ 2 / 12 ]

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Alan slept for the entire drive back home, since he was exhausted from all the sexual fun.

When the group did get back, it was already quite dark and past dinner time for most people. Suzanne and Amy had to go back to their own house to spend time with the men of their family.

Alan was still very tired. He rested some more while Susan told Katherine all about the beach trip. (Susan wasn’t rubbing in the fact that Katherine couldn’t go; she just loved to share her experiences.)

However, as tired as Alan was and as full as his weekend had been, it still wasn’t over. He was scheduled for his second “non-romantic” date with Christine. Since he’d already canceled and rescheduled it on Friday, there was no way he could push it off again. He was glad that at least he was sufficiently rested for that.

Susan teased him about his “hot date.” She seemed to think it was an established fact that Alan and Christine would become sexually involved, so she dismissed all his protests that this was just a “practice date.”

Katherine, on the other hand, gave him a lot of grief about it. While she liked Christine well enough from a purely objective point of view, she burned with jealousy whenever Alan did anything with her.

Alan was relieved when he was finally able to leave the house.

He’d already promised Katherine that he wouldn’t go to the movies with Christine, and he intended to keep that promise. So when they’d made their plans, he’d asked Christine what she wanted to do instead.

She’d replied, “Like I told you last time, I never get to go out on dates because I have to remain focused on school. But I had a lot of fun last time getting all dressed up and making a big deal of it. Why don’t we do that again, but get even dressier? We can dress to the nines and go out to a nice restaurant. That’ll be enough for me because Monday’s a school day. What do you say to that?”

Alan had agreed. He dressed up in the nicest clothes he owned, which meant he wore a suit and tie, as he had done only a handful of times before in his life. He wasn’t happy about having to do that, but the restaurant that Christine had picked, The Avalon, was the fanciest one for miles around and it required all men to wear a coat and tie.

He’d been impressed with Christine’s nice outfit when he picked her up for their last date, because she usually wore nothing but nondescript, conservatively cut clothing at school. But he was absolutely floored when he arrived to pick her up this time. She was wearing the kind of fancy black outfit that would be perfectly appropriate for a meal at a fancy restaurant like The Avalon, but it also looked like an ideal outfit to show off the goods of a high-priced call girl.

He took one look at her, and his jaw nearly dropped to the ground. Are you kidding me?! Are you friggin’ kidding me?! She’s soooo hot! Just look at that cleavage! Jesus Christ, it’s like ten miles of cleavage! Dang! Instant boner! How the hell am I going to make it through this date when she’s dressed like that? Talk about blue balls city. And what’s amazing is that she’s dressing like that for ME! Nobody else gets to see her in all her busty glory except me!

And she’s not even my girlfriend, and now it’s too late for her to ever be. Fuuuuck! I feel like this is almost some kind of cosmic test, to see if I’m morally worthy of having all these lovers. I can’t give in to my lust and bring this pure angel down into my sordid world. I can’t!

Christine was blushing and nervous as Alan walked up to her. Before he even got a chance to speak, she said, “I don’t own any nice dresses myself. I borrowed this, and it’s a little bit more daring than I would have liked.” She fidgeted nervously and shifted her feet back and forth, which inadvertently set her breasts jiggling. “Okay, a lot more daring.”

Even though Alan had been surrounded by naked breasts and entire naked bodies for the entire afternoon, the sight of Christine’s deep cleavage got his dick hard in a heartbeat.

He thought, Holy hell! As if I’m not aroused enough already. I must be some kind of wicked person, because seeing her all shy and blushing is doubly arousing! It’s like she’s got the sultry body of a super elite call girl with the face and mind of an angel! Dang! She’s showing so much cleavage, is it even possible for her to be wearing a bra with that?! I just wanna… I wanna kiss and caress her so bad!

He realized that he was staring too long and too obviously. He needed to do something to break her nervous mood. The song “You Sexy Thing” by Hot Chocolate popped into his head, so he sang,

“I believe in miracles.

Where you from, you sexy thing?

You sexy thing, you.

I believe in miracles,

since you came along, you sexy thing.”

Christine had a good laugh, which helped to dissipate some of her nervousness at wearing such a daring outfit. The song was old, but it was famous enough so even she knew it. She thought, This is why Alan is great. He makes me laugh, and makes me feel really good about myself. 𝓫𝓭𝓸𝓋𝓁．𝓬𝓸𝓂

However, he could tell she was still a bit jittery, so he continued to play it cool. Smiling, he said, “No worries. I think you look great!” Trying to imitate Billy Crystal, he joked, “Daaling, you look maahvalous!”

She smiled in return. “Really? You’re just saying that.”

“Christine, pardon my French, but holy fucking Jesus H. Christ son of a bitch! Oh my God, you are SCORCHING! If you were any hotter, I’d seriously be afraid to touch you because I wouldn’t want my fingers to burn off!”

She laughed. “Okay, now you’re really laying it on thick.” She added in a husky voice, “Sounds like we may have a problem though because I certainly want you to touch me.”

He thought, Whoa! Warning alert! Danger, Will Robinson, danger! Is she giving off a sexy vibe or what?! This is not what I expected.

She took his hand as a friendly gesture before speaking.

But before she could, he pulled his hand away. He waved it around with a pained expression on his face, like he’d just touched a hot oven. Then she realized he was hamming up his comment about her being too hot to touch.

She laughed heartily, and the rest of her nervousness faded away. “Very funny, wise guy.” She was trying to act chagrined instead of amused, but she couldn’t stop chuckling.

He patted his clothes, as if looking for something.

“What?” she asked.

He was still pretending to check his pockets and so forth. “I’d anticipated this, because I’m well aware of what a hottie you are. So I made plans to bring oven mitts. But I seem to have misplaced them.”

She chuckled some more. “Come on, you brunette bozo.” (Due to what he’d started with his dumb blonde jokes, hair color references were a kind of friendly insult.) “Let’s get going before I freeze to death. This napkin I’m wearing doesn’t exactly keep me warm.”

He took her hand, while acting extremely apprehensive about it. This time, he pretended surprise that his hand didn’t burn off. “Hmmm. Maybe I’ll be okay after all. I’ve sort of built up a tolerance after being so close to your hotness every day in school.”

They started to walk away. She was going to modestly tell him to lay off the hotness jokes. But before she could, he stopped and stared off into space with a strange expression. “What?” she asked.

He stammered, “I feel a… feel a… sneeze… coming on… can I borrow your napkin?”

She remembered her comment likening her outfit to a napkin, and had another good laugh. But then, mindful of her plan to act more flirty, she said in a sultry voice while looking around nervously, “Okay, but here. Let’s get to a private place, and then you can take my clothes off.”

He jaw nearly fell off again. He stared at her in sheer confusion. He was certain she couldn’t mean it, but then again, she didn’t tease like that, ever, so could she possibly mean it?!

She let him suffer for a few seconds, and then smiled. “A-ha! Got you! Two can play the teasing game, you know.”

He laughed, and felt strangely relieved. Phew! Not even I could be that lucky for her to actually mean it. And if she did, what would I do?! I’d have to say no, but would I mean it and stick to it?! Let’s hope it never comes to that! He said, “Man you got me. You got me good.”

They resumed walking. She said, “You know, one thing I like about these dates is that we can flirt without any worries that it’ll go anywhere. I can even say something outrageous like that. It’s kind of like flirting with training wheels on.”

“Yeah, that is cool.” He thought, Phew! She was freaking me out for a minute there. I thought she was coming on to me or something. Especially with that incredible black dress. Man, I never thought I’d live to see the day where I could see ALL of Christine’s cleavage, but there it is in all its glory! Woo-hoo! And it’s just as perfect as I’d imagined. The only thing that would make that a prettier picture is if my happy hard-on was in the frame, plowing up and down her busty valley.

Whoa, Nelly! Calm down boy. This is no way to start a non-romantic date, with a raging erection to end all raging erections. Think of something else!

He tried to follow his own advice, but his mind wanted to think about things like Suzanne’s or Susan’s cleavage, comparing and contrasting their busts to Christine’s. That was only making his problem ten times worse. Are her nipples erect? I think they are. Hell, in that dress it’s totally obvious that they are! Could she be that aroused because of me, or is it the cold, or just wearing such a revealing dress?!

Christine left him to his thoughts for a few moments, then said, “By the way, thanks for the compliments. I should mention that you look great too. Seeing you in a suit makes my heart go pitter patter. When you drove up I was asking myself, ‘Where’s Alan, and what’s Cary Grant doing here?'”

That broke him out of his reverie. “Yeah, right. Now you’re the one laying it on thick. But you’re right: talking like this is fun.” He’d been holding something behind his back with one hand the whole time, and now brought it out. It was a bouquet of a dozen roses. “Here, my lady, these are for you.”

Christine squealed with delight, took them from him, and smelled them. Her face lit up with a grand smile since, unlike most hothouse roses, the florist had found some for him that were actually fragrant. Then Christine leaned forward and kissed him on the cheek.

She had actually intended to kiss him on the lips, but she chickened out at the last moment. That was one of her problems: because she was completely inexperienced sexually, she had very low self-confidence with such matters and had never developed any real flirting skills. However, she tried to make up for it by letting her lips linger on his skin while also giving him a partial hug.

When she pulled back, she said, “Thank you! I’ve never been given flowers before. These smell so nice. You’re gonna get soooo lucky tonight!”

His jaw nearly hit the floor.

Then she winked and added, “Of course I mean that in a completely platonic way.”

“Of course. Ah. Flirting practice. Fun.” But for a few seconds he’d thought she’d really meant it, and his heart was racing a thousand miles an hour. Man, this is nuts! First, saying she wants me to touch her, then offering to take off her “napkin” dress, and now this. Good grief! I think she’s trying to give me a heart attack! If it wasn’t for the fact that I’m so used to being around all my lovable hotties at home, I’d melt from all the sexual heat radiating from her. Anyone would!

Calming himself a bit, he joked, “You know, those flowers cost extra. Knowing that you’d touch them, I had to buy the flame-proof kind.”

She laughed. “I didn’t know there even were ones like that.”

“I didn’t either, but just the same, you’d better put them down before they spontaneously burst into flames.” He took her by the arm in a gallant fashion, and said, “Come, my lady. Let’s go paint the town red.” He opened the car door for her and generally behaved like a perfect gentleman.

As he started the car, he thought to himself, Man, if it’s gonna be like this all evening long, I seriously don’t know if my heart can take it. Flirty Christine is almost scary! She just looks too smoking hot to resist! I never thought I’d say this and mean it, but… hubba hubba hubba! Hot damn!

Had he known what Christine was thinking, he would have been even more blown away. She’d been coming around to the idea of getting romantic with him after all. Although she was all but certain that he was dating Amy and Kim as well, at the very least, she figured that she had a good chance of winning any competition with any other girl if she just put her mind to it. She knew she had an incredible body, with a face to match, and was smart as a whip and all-around talented to boot.

She’d always liked him a lot, but mostly just as a friend. However in the past couple of weeks he’d become a new person in a lot of ways: much more assertive, easy-going, and generally happy (thanks to all his new sexual experience). That unaffected self-confidence made a big difference as far as the ladies were concerned.

She was hardly the only girl in school looking at him in a new light, especially with all the rumors going around in certain circles. She felt like she had to push the boundaries of the practice date or she’d fall too far behind the competition.