Six Times A Day
Part 42: Long Cool Woman in a Black Dress

Copyright© 2004 - 2015 by Spacer X. All rights reserved

Harem Incest Sex Story: Part 42: Long Cool Woman in a Black Dress - High school senior Alan is diagnosed with a rare condition requiring six orgasms a day. The women in his life - mother, sister, neighbors, cheerleaders, and more - end up swept away by their own lusts while helping him. This epic roller coaster of passion, love, and sex leads to results no one sees coming. The variety of characters, humor, and hot sex will leave you wanting more.

Caution: This Harem Incest Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   mt/Fa   Fa/Fa   ft/ft   Fa/ft   Mult   Consensual   Reluctant   Romantic   BiSexual   Humor   Incest   Mother   Son   Brother   Sister   Daughter   Group Sex   Harem   Polygamy/Polyamory   Anal Sex   Exhibitionism   First   Lactation   Oral Sex   Sex Toys   Voyeurism   Big Breasts   Doctor/Nurse   Size   Slow   Illustrated   mother helps son relieve his blue balls,mother sucks son,mother fucks son,sister fucks her own brother,sister tricks brother into sex

Day 56: Sunday, November 10

Chapter 1

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 in a tight, dark dress with arms under her breasts, showing off her prominent rack

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.

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.


Chapter 2

But much to his relief, the two of them had a nice meal and enjoyable conversation at the restaurant. They had a great many "nerdy" and intellectual interests in common. It was true that Christine wasn't into popular culture to the extent that Alan was, since she spent so much time with her schoolwork, martial arts practice and such, but her favorite movies and TV shows were almost exactly the same as his. The only area where they didn't find much common ground was music, since Alan loved rock and roll and Christine was more into classical.

They laughed, gossiped and bonded.

Alan couldn't remember the last time he'd had such a fun (not to mention delicious) meal.

Christine looking totally gorgeous

The only problem Alan had was that Christine looked so gorgeous. His erection was almost continuously hard, which became a problem because the meal lasted three hours. Every now and then he would get distracted and start to lose his erection, but then he'd really look at her and find himself not only painfully aroused, but on the verge of falling in love with her all over again.

It was difficult enough that she had such an impressive and sizable chest, enticingly displayed by her stunning dress. But when he tried not to stare at all of that cleavage on display he'd find himself staring at her face and her hair, and that was just as impressive and arousing in its own way. There was no denying that she was a real head turner.

At one point, Alan said, "Okay, forgive me if I'm being nosy, but I just have to ask. Your dress is amaaaazing! So very, very sexy! But you mentioned that you borrowed it. From who? How? There must be a story there."

She blushed slightly as she explained, "Ah, you see ... I have this aunt, named Kirsten. Even though she's my aunt, she's not that much older than me, so I think of her more like a cousin, or even kind of the sister I never had. Anyway, she lives in the area, and she runs her own modeling agency; she actually used to be a model herself. So she's got all kinds of clothes. To be brutally frank, I don't know a thing about fashion, so I kind of turn to her for help. This actually is one of hers."

Alan replied, "Ah. I see."

On the surface, there was nothing particularly embarrassing about that, so he didn't understand why she had blushed. He decided it wouldn't be polite to ask.

The reason Christine blushed was because that wasn't the full story. When she'd told Kirsten that she wanted some very sexy clothes, as well as advice, Kirsten was glad to help, but she'd also playfully teased Christine quite a lot. She knew Christine had never been on a date before, "practice" or not, and thus this had to be a very big deal for her. As a result, she'd asked all kinds of questions about Alan and Christine's feelings for him.

Furthermore, the truth was, Kirsten had a great many dresses. Christine had selected one of the most outrageous ones, with a scandalously low neckline, because she'd caught Alan staring at her breasts so often and wanted to please him. She was also well aware that he was involved with at least Amy and Kim, and she felt like she had to outdo the competition. Recalling her dress selection, and the way Kirsten had razzed her about it, embarrassed her.

Instead of prying further about that, Alan said, "If Kirsten is your aunt, and she used to be a model, and she fits into that dress you're wearing, then she must be a total stunner! But I'm not surprised, because great beauty obviously runs in your family."

Christine's blush deepened at the obvious compliment. She turned her head and mumbled, "I don't know about that."

He asked, "If you two are close, how come I've never heard about her?"

Christine was able to recover and resume eye contact, since that put her back on solid ground. "No reason, except that she doesn't go to our school, and it seems we've always just talked about school-related stuff. To be honest, there's a lot of things about me you don't know."

"I'm sure that's true, and probably ditto with me. But that's why dinners like this are so good: we can get to know each other better, beyond all that school stuff."

Following that, they asked each other questions about their respective families and childhoods, and other matters they'd never talked much about previously, all the while keeping their mood light and fun.

They were more open and inquisitive about each other than ever before. For instance, at one point, Alan asked, "Okay, truth time. I've got a question I've been meaning to ask you since forever."

"What's that?"

He thought, What did your parents feed you growing up that put all your weight in your breasts and other curvy spots?! But instead he settled on asking something else he'd long wanted to know: "What's the story with your hair? I mean, it's pretty obvious that you dress and act to minimize attention. You certainly aren't looking for random yahoos to shout come-ons at you. But your curly locks down your front and your very long hair down back, that draws attention like nobody's business. Especially because you have such gorgeous blonde hair. Is there a story behind that?"

She replied honestly, "As a matter of fact there is, although I wouldn't call it much of a story. It's a long family tradition on my mother's side. My mother Olga has these curly locks and long straight hair in back, and her mother in Norway did, and her mother did, and so on, as far back as anyone can remember. I'm not crazy about it, to be honest, because you're right, I don't like the attention it brings me. But at the same time, I'm kind of proud to be carrying on a family tradition."

He nodded. "Ah. Cool. That's pretty neat, actually. Who knows? Maybe if you go enough generations back, there's an axe-wielding Viking berserker named Kristina rushing into battle with blonde, curly locks. Didn't Viking women fight along with the men?"

She smiled. "They did. And you know what else? Berserkers had a habit of going into battle naked to shock and intimidate their enemies." She winked playfully.

"Whoa!" He sat back with wide eyes, overcome with a vision of Christine as a nude Viking warrior. "Man. You shouldn't have said that. Now, I'm never going to think of the Vikings in the same way again." He shook himself from his reverie, and said playfully, "Hey you know all those historical re-enacter types, who reenact Civil War battles and such?"

"Yeah? Somehow, I think I know where you're going with this, but please proceed." She was smiling and having lots of fun.

"You should totally get involved with that! If you did, participation would shoot up a thousand percent!"

Christine

She chuckled. "Actually, that could be kind of fun. I'd have a plastic axe and use it to wound rather than kill, so any guy who looked at my bare breasts in a lusty manner would get thwacked to the ground! I could release years of pent-up frustration from all the leering and cat-calls I've had to endure. Right in the neck!" She pretended to swing an axe.

He sat back, as if getting out of range of her axe, and dropped his smile. "Um, on second thought, maybe that's not such a good idea." Trying to change the subject slightly, he asked, "By the way, do you feel any affinity with your Viking ancestry? Or your Norwegian background in general?"

"Nah. Not really. The Vikings were a thousand years ago, anyway. My parents do, but I've been heavily Americanized, to their regret. I don't usually read or write the language, though we do speak it at home sometimes. I've been to Norway, but it's only been for a couple of short trips to visit relatives. It didn't feel like home to me at all. This is home."

She was going to ask him about his affinity for his background, but at the last second she remembered that he was adopted and didn't know what his background was. So instead, she said, "Since we're asking questions we never felt we could ask until now, I've got one for you."

"Shoot."

"This isn't just for you, but for men in general. Although it's especially for you. What's the deal with the male attraction to breasts?!"

"What do you mean?"

"What's so fascinating about them? I know they give me a certain power over guys. I could move in a certain way that'll make a guy turn into a blithering idiot. It's a blessing and a curse. But you're basically my one male friend, and it's not something I could ask my dad. You're a self-confessed 'tit man.' What exactly is going on in your head at times like that?"

He searched his feelings, trying to give a sincere and serious answer. After a long pause, he said, "I don't know. It arouses me in a big way, but I don't know why. I wish I knew, because it's frustrating not being able to explain or control it. It must be a hard-wired, biological thing. Totally speaking out of my ass, since I've never looked into this, I'm guessing that anything that makes a woman different than a man becomes a turn-on, and vice versa. For instance, a male hairy body can be a positive, but it's a huge turn-off to see a hairy-bodied woman. Part of it is cultural, I'd guess. I'd bet that if most women shaved their heads bald in a certain culture, that would be a huge turn-on for guys. And the more the difference is, the more arousing it is. So, big breasts are more arousing than small ones." He shrugged.

"I've never looked into the research either," she replied. "But that makes sense. But is that all there is? For instance, asses don't really look that different. If you took a photo of just a person's ass and it wasn't hairy, you'd be hard pressed to tell if it belonged to a man or a woman. But that's a turn-on too, isn't it? Or is there something extra-special about the breasts?"

"I think there is something special about the breasts that's hard-wired," he replied. "Maybe it has to do with wanting to see if the mother would be able to lactate for her babies? Could it be a sign of fertility and good health?"

"Probably. That makes sense to me."

He nodded. "But who knows for sure? Again, speaking of asses, all my ideas on this are coming straight out of mine. But also, and this is something I'm glad I can finally tell you face to face ... There's one very important reason I joke with you a lot about your breasts: it's safe!"

She raised a curious eyebrow. "Meaning?"

"Meaning ... there are other body parts ... the vagina, for instance ... that are SO taboo that, well, they're really taboo. Maybe other guys would be cruder and tease you about that, and your ass for that matter, but that's not me. That seems over the line to me. Heck, it's weird for me to even say that 'V' word to you. But breasts are relatively tame, I guess." He frowned with uncertainty. "I don't know. Maybe I'm way off. But I've long felt that, with you, I could joke about your breasts and it doesn't mean I'm a total perv. Just a partial perv."

She grinned at that. "The jury's still out. I think you're leaning towards 'total perv.'"

He grinned back, knowing she was just teasing him. "There's also the fact that they're so very prominent on you, and big breasts are overwhelmingly considered a desirable thing to have. It's like gently teasing a really tall guy about his tallness. That's all in good fun if done in the right way, but doing the same about how short a short guy is wouldn't be nice at all." He asked anxiously, "But AM I way off? IS that something that bothers you? Geez, I should have asked you this a year ago, at least!"

She carefully considered her answer. "To be honest, when you started joking about that, way back when, it did kind of annoy me at times. But I grew to like it, and to even look forward to it. You amuse me, and it is flattering in a weird kind of way, with the way you do it. Mind you, if someone else were to joke like that with me, it would totally bug me. And I see what you mean about it being relatively safe. For instance, you've joked a thousand times about wanting to touch them, but you've never actually tried to, not even once. I trust you. And I guess that's what a lot of humor is, poking at something that's a little taboo, a little risqué, but not too much. It helps to have that slight sense of danger."

He smiled with relief. Then he joked, "Yeah, but after a while that sense of taboo or danger wears off, so one has to raise things up a notch. I propose that in the future, when I make a joke about your breasts, that I actually fondle them at the same time."

She snorted with laughter. "Yeah, right! You wish!"

He held his hands up defensively. "Mind you, it would be purely for humorous effect only. It wouldn't be like I'd enjoy that at all. I'd just be doing it ... extensively ... for a laugh. Very extensively. Some jokes require a loooong set up."

She laughed some more. "You're a crazy nut!" In truth, she loved this kind of banter, and she hoped it would eventually lead to more.


Chapter 3

After that, their conversation grew more serious. For a while, there wasn't a lot of flirting or teasing, especially while they ate their meal.

But that changed as they finished eating the main course. Christine looked around the restaurant conspiratorially, and then leaned forward like she was going to tell him an important secret. She commented, "I wonder what people would think if they saw us here together."

"What, you mean like people at school?" When she nodded he shrugged. "I suppose the rumor mill would have a field day."

"I think it would. Especially since there's all kinds of rumors about you already."

She'd warned him of some rumors before, but still he played coy, with silly, obvious exaggeration. "Me? Little ol' me? Nobody wants to know about a nobody like me."

She smirked. "Yeah, right. Did you know there are even MORE rumors about you lately? And they're getting wilder all the time."

"Really, like what?"

"To tell the truth, there's only one new rumor, but it's quite a doozy. The word is that someone who looks very much like you was seen having sex with a completely naked blonde in the teacher's parking lot during school. Can you believe it?" She laughed heartily. "As if that isn't crazy enough, they say the girl had a long ponytail and a deep tan, just like Heather!"

Between the way Christine was leaning forward and the way she was laughing, it seemed her heavy boobs would escape her dress altogether. But Alan couldn't enjoy the view because he was so frightened by this latest 'rumor'. He realized someone must have seen him and Heather fucking in the parking lot on Friday. He'd been convinced there was no one around, but someone must have seen them anyway, if only from a considerable distance.

He was lucky that Christine apparently dismissed that rumor because she thought it was simply too outrageous. As a result, she was busy laughing instead of closely scrutinizing his face for tell-tale reactions, which he certainly was having. That gave him a few seconds to recover and join in her laughter. "Boy! You're kidding me! Me and HEATHER? Naked in a school parking lot?!"

"I know!"

As the laughter died down, he deadpanned, but in an obviously joking manner, "It's true though. The reason we did it in the parking lot is because that's where she parked her flying saucer. After we did the deed, we took off and flew to her secret moon base."

 
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