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DATING MAGGIE Prologue
DATING MAGGIE
Prologue: Hillary and Maggie

(mF, mf, Ff, mult, cons, reluc, humor, cheat, inc, mother, D/S, Mdom, span, lght,
  humil, group, orgy, poly, WC, WM, WF, oral, exhib, toys, BBR, slow)

Written by Spacer X <paul_t_22@yahoo.com>

Copyright © 2014 - present Spacer X; All Rights Reserved.

Nick was obsessed, doubly obsessed.

His first obsession was a high school classmate named Hillary. She had a body to die for: huge and shapely breasts, long muscular legs, a perfect bubble butt, and a face that was somehow both sultry and girl-next-door innocent. The thing he liked most about her face was that she was almost always sporting a big smile, reflecting her inner happiness and natural kindness.

But her looks were just one part of why he was deeply in lust and love with her. She was smart - incredibly smart, in fact. Like him, she was 17 years old and just starting "Advanced Studies," a program for a small number of very gifted students that was on an even more advanced track than the usual gifted track.

One thing that made Hillary stand apart was her "hippie chick" personality. She had hippie parents, and one could see some of the "hippie" in her too. Her dress style was extremely casual, as if she didn't care at all about what people thought of her. Sometimes, she even wore tie-dye shirts, which was almost unheard of in Nick's school.

Despite her stellar academic record, she wasn't any kind of geek. There were many stories and rumors about her wild side. For one thing, it was well known that she liked to get high. It seemed to be a legacy from having hippie parents, especially since she only showed interest in "hippie drugs" like pot, LSD, and mushrooms. She loved rock and roll and was musically talented on top of everything else. She also had a "hippie" taste in music, loving classic rock from the late sixties most of all.

She was openly bisexual, and proud of it. She considered herself equally attracted to both sexes. She dated girls just as often as guys, and didn't sneak around to date girls either. A lot of people in the area where they lived - Orange County, California - especially parents and teachers, frowned at her defiantly open bisexual stance. Not surprisingly, images of Hillary getting it on with other women filled Nick's fantasies.

It was also clear that she had a very active sex life. It seemed she was always dating somebody: if it wasn't a handsome guy, then it was a gorgeous girl. There were rumors of her taking part in orgies, gangbangs, and who knows what else.

Whatever Hillary did, that's what Nick wanted to do too. Whatever she liked, he liked. He worked hard at school so he could be in the same gifted classes as she was. He jogged almost every morning, even though he hated it, just because Hillary did it. Hillary lived nearby, and sometimes when he got lucky they would cross paths when she was jogging.

However, Nick wasn't some kind of stalker. In fact, he was just the opposite. He appeared to pay no special attention to what was happening to her when he sat near her in class, which was most of the school day. But other than the classroom interactions expected of him, he went out of the way to avoid interacting with her. It wasn't that he wanted to, but he was shy and even afraid of her. She knew his name well, because of the classes they shared together, and they said "hi" or "what's up?" or the like to each other every now and then. But that was it. Having to actually talk to her beyond the "Hey, how are you doing?" level was absolutely frightening for him.

Hillary was only Nick's first sexual obsession. If anything, he was even more obsessed with his mother Margaret. When he was at school he would endlessly obsess about Hillary, and then he'd spend the rest of his hours at home obsessing about his mother. And the two were interrelated, because Hillary and Margaret shared many similarities.

Most obviously, they looked very much alike. Like Hillary, Margaret was a complete knockout. And also like Hillary, she didn't seem to be aware of that fact, or at least she didn't let it go to her head. Margaret was just a normal mother, doing normal motherly things. The fact that she had a body that could easily grace the cover of Playboy or feature in a porn film was something that took him a long time to appreciate as he was growing up. Only when he hit puberty did he start to realize that she was more than just a soccer mom with above-average looks - she was totally hot!

Margaret and Hillary had the same curvy but fit physiques. Margaret worked out religiously, and as a result her looks completely defied her age. Nick had surreptitiously checked Margaret's bra size once, discovering that she wore E-cups (on a scale that included double-D cups). After countless hours of furtive staring across classrooms, he decided Hillary wore the same size, or perhaps even larger.

Their faces were very different, but they both had that sexy-yet-innocent look that really aroused Nick. Both radiated health, happiness, and wholesomeness.

They even had the same shade of brown hair, although Hillary kept hers long and straight while Margaret kept hers short and a bit curly. They both had brown eyes. Their nice tans with rosy cheeks suggested they spent a lot of time out in the sun.

Technically, Margaret was Nick's second overt obsession, not his first, because he'd felt a strong attraction to his mother for a long time. But he didn't consciously realize it or allow himself to "go there," so he'd been projecting those feelings onto Hillary from the start of junior high. Only much later, around the time he started high school, had he allowed himself to masturbate about his mother.

Even then, he long denied that Oedipal attraction as much as he could. Yet slowly but surely, his feelings for her had developed into an undeniably full-blown obsession. She was simply too sexy to resist! Like Hillary, she dressed down in a casual style, but there was no way to completely hide her voluptuous curves.

Nick's obsessions left him profoundly unhappy. He didn't have the guts to approach the very popular Hillary at school. Worse, any thought of doing something sexual with his mother at home was completely out of the question. He was a virgin in every way. He had never even been on a date or kissed a girl, because he had no interest whatsoever in anyone other than Margaret or Hillary, and both of them seemed hopelessly out of his reach.

Nick's parents Margaret and Andy had seemed to have a typical marriage up until two years earlier, when two pivotal events happened in quick succession. First, Margaret discovered that Andy had been having a long-term affair with a neighbor. Andy was quite a handsome and charming man, which helped explain how he'd won Margaret in the first place. But even though their marriage had been a happy and sexually active one, he couldn't resist using his charms on others.

Margaret was devastated. But Andy was too, since he really loved his wife, yet thought he could cheat without major consequences.

The second pivotal event quickly followed. The night Maggie found out, he went driving in a nearly suicidal mood and ended up in a terrible car crash. Miraculously, he was pulled out of the tangled wreck still alive, but his legs were never the same after that.

He walked with a cane thereafter, wobbling and limping painfully with each step he took. He couldn't go up or down stairs, and he often got around the house by rolling an office chair over the hardwood floors. He could still ride in a car as a passenger, but he preferred not to leave the house unless he absolutely had to.

The accident put Margaret in a fix. Had it not been for his injuries, she would have divorced him since his cheating wasn't just a drunken one-night stand or something like that. His affair had gone on for years. To make matters much worse, it soon came out that it wasn't the only affair he'd had. However, with Andy so severely injured, she felt obliged to take care of him.

Somehow, Margaret and Andy's marriage limped on, but all the love and trust was gone. They mostly stayed together because they thought it would be better for Nick. But it was more like they were roommates instead of spouses. They agreed that their marriage was effectively over; and the only reason they were delaying their divorce was so that their family would continue to live together until Nick graduated from high school. Rather than argue and fight all the time, they kept their emotional distance from each other and lived generally unhappy lives.

Margaret had no intention of resuming sexual relations with Andy, due to all of his cheating. But it turned out even that was impossible, because Andy had also been made impotent by the accident. While he still had all his equipment, he could no longer achieve an erection. He might have gotten better, but he had grown so depressed and sullen that he refused to take part in any physical therapy. Luckily, he had a job that he could do from his home computer, otherwise he probably wouldn't have been able to work at all.

Although Maggie and Andy slept in separate bedrooms and didn't have much to do with each other anymore, Andy still selfishly used Margaret as his maid and cook, leaving her very unhappy with the situation. But, due to his injury, she took pity on him.

Andy and Margaret had always hidden their sex lives from their son, so it took a long time before Nick had even realized what was going on. Although he knew something terrible had happened around the time of Andy's accident to tear his parents apart, he had not learned of Andy's history of cheating. He also didn't know about Andy's impotence. He'd only overheard cryptic disparaging comments about his father from his mother's friends, when they thought they were talking with her in private.

Then one day Nick overheard a conversation that changed his life. Margaret was conversing with her best friend Sally in the living room, and neither of them realized that Nick had wandered into the adjacent kitchen for a snack. He was always aware of Sally's presence, because she was his friend. And it didn't exactly hurt that she was quite beautiful.

After a couple of minutes, Sally got to the heart of the matter and said to Margaret, "When are you going to get off your ass? I understand you stick with Andy because of Nick, but Nick is nearly an adult now. He's going off to college soon, and then what? Will you STILL stay with Andy?"

"No," Margaret replied. "No way. You know I told you that already, and I'm more determined than ever. This dead marriage is slowly killing me. Andy knows we have no future, and he's resigned to it."

"Well then, you need to start looking NOW! Get a grip! Start dating already. What are you waiting for?"

"You know what I'm waiting for," Margaret testily complained. "As long as I'm married, I intend to honor my marriage vows."

"But Andy-" Sally started to say.

"I know, I know. He certainly didn't honor his vows. He cheated, lied, and betrayed my trust repeatedly. But so what? If he took drugs, does that mean I also have to? I would be a hypocrite after what I've said to him about his cheating if I were to go and do the same thing myself."

Sally complained, "But it's totally different! For one thing, he can't even get it up anymore. You haven't had any sex in TWO YEARS! Hell, I can't imagine going two weeks, let alone two whole years. But more importantly, he's GIVEN YOU PERMISSION! He actually said he'd honestly prefer that you have affairs rather than being forced to remain celibate because of the mistakes he made. He'd feel less guilty about that. Come ON! The only caveat is that you be discreet, so he doesn't have to know. So what are you waiting for?"

Margaret didn't reply.

Sally sighed with frustration, then continued, "I keep pointing this out, and you keep bringing up your 'honor your marriage vows' crap. You're gonna lose out and miss the man of your dreams. You won't look young and hot forever, you know. Besides, you're totally miserable. Sometimes I honestly want to slap you silly because of your stubborn attitude. Isn't there ANY scenario where you could at least sate your sexual urges so you aren't moping around all the time?"

Margaret considered that carefully, then said, "If I could find a guy just like a human dildo, someone I could have sex with without any strings attached, I'd go for it in a heartbeat. But there are always strings attached. Finding the right guy who could be discreet about that would be a huge challenge. I wouldn't want to be vindictive and throw my affairs in Andy's face. Two wrongs don't make a right. And then I wouldn't want Nick to know. So discretion would be key."

She went on, "But even if I found a discreet lover, that would just create a whole lot of new problems. He could get too attached to me. Or I could get too attached to him. There are sexual diseases to worry about. And on and on. And I'd have to change partners frequently or we'd develop at least some emotional attachment no matter how hard we fought it. So I'd go through the same hassles over and over again. It's just not worth it. My trusty dildo does me just fine, thank you very much."

Sally pointed out, "But you WANT to develop emotional ties. If you'd break your marriage vows anyway, then find yourself Mr. Right! Why wait?"

Margaret groused, "But it's different. It was the obvious love between Andy and his primary girlfriend that really killed me. That hurt me way more than all his other lovers combined. I wouldn't wish that kind of pain on my worst enemy, not even Andy. He's already a beaten man due to his injuries. I'm not going to kick him when he's down. I can wait a little longer until Nick graduates from high school; then I'll get a divorce and start living my life again. I've been staying in tiptop shape and working on an all-over tan. When the time comes, I'll be ready to hit the ground running."

"The time is NOW!" Sally complained. But when she didn't get a reply, she asked a bit shyly, "Wait a minute. You're working on an all-over tan? Seriously?"

Margaret said proudly, "I should rephrase that: I have an all-over tan already. You know how bored I am most of the day. Well, while Nick is in school, I go to our sun roof. There's perfect privacy up there, and of course Andy can't go up there due to his injured legs."

"Wait. So you get totally naked outside, every single day?!"

"Some days. It's been hard to find the time this summer, since Nick is home so much, but I manage. It's kind of fun. And my tan-lines are long gone!"

From Nick's perspective, the conversation went off on a tangent about tans from that point.

Shortly thereafter, Nick managed to steal away without being discovered. He was so horny with thoughts of his mother naked and tanning all over, plus excited from everything else he'd learned, that he rushed straight to his room to masturbate - twice. He had a curious tendency to "cum in twos," as he called it to himself, because he would typicaly stay erect after cumming the first time but always go flaccid after cumming the second time. He also just tended to masturbate a lot, cumming about four to six times a day.

It took him a while to process all of that shocking news. Nearly all of it was news to him, even though he'd already guessed that his dad had cheated, since it was the best explanation for his mother's coldness to his father.

He'd long suppressed his lust for his mother, figuring the odds of them ever getting intimate were beyond impossible. Even if it weren't for the age difference, the incest, and the fact that she was still respecting her marriage vows, he felt he just wasn't that handsome. There wasn't anything wrong with him; he was just ordinary by many measures. For instance, he was five foot nine - only an inch taller than both Maggie and Hillary - and of average weight and muscularity for his age. He didn't stand out in any way except for his intelligence, but he felt that his being smart reduced his attractiveness to girls rather than helped.

By and by, he came to think: Why not me? If Ma were to have sex with me, she wouldn't have to worry about all those problems. In fact, I'm the one person in the world who could be a reliable sex partner for years to come without having to worry about the attachment problem. And I'm right here in the same house - it would be so perfect!

But then he reconsidered. No. She's my mom. My fuckin' MOM! That's so wrong! It doesn't matter how hot and sexy she is; she's still my mother. Dammit! Dammit! She'd never be willing in a million years.

Life is so cruel. Why the hell do I have to have a mother who's simply the most arousing woman on the entire planet? I can't even hear her name mentioned without getting a hard-on. And now to find out she's not having sex with Dad... It's like God is fucking with my head just to torture me. Damn!

From that point on Nick actively fantasized about really having sex with his mother. The fact that there was at least a remote possibility something could actually happen made his masturbation sessions much more arousing and emotionally powerful than ever before.

He was surprised at how little guilt he felt about it. He worried that she would disapprove, but he didn't care much about how his father Andy felt. Partly that was because he'd lost so much respect for Andy after finding out that he'd been a multiple cheater. But as time went on, Nick realized more and more that Andy had stopped being a good father long before he'd been exposed as a cheater. Andy had been a very good father when Nick was young, but around the time that Nick hit puberty, Andy had started to withdraw, seemingly losing interest in all father-son-related activities. It was at that same time that Andy had become a much worse husband to Nick's mother.

Nick didn't understand why that had happened, and because he'd grown so distant from Andy he had never even felt like asking. It was easier for him to just keep a distant truce going, presumably until he graduated and moved away. But Nick had his own theory as to the cause: he believed that Andy had become distant around the same time that he'd established a serious romantic relationship outside his marriage, causing him to put more time and energy into his illicit affairs than with his family.

In hindsight, Nick wondered whether his father had been running away from the pressures and responsibilities of being a father and husband, because that's exactly how it looked to Nick. After a year or two of Andy's growing increasingly distant attitude, things reached a point where Margaret had essentially raised Nick all by herself.

The only things Andy still did with Nick, beyond eating meals together as a family, were things that Andy liked to do anyway. Their one big common interest was a love of football, so father and son would watch football games together on Sundays during football season. But that was about it.

At first, Nick was deeply hurt, but over time the wound scabbed over and he grew more indifferent than hateful.

It helped greatly that Nick's mother had stepped up and always been there for him, essentially serving in the roles of both mother and father. After Andy's cheating revelation and accident, that process had accelerated further.

Because of all these events, perhaps it wasn't surprising that Nick's love for his mother was especially intense. And due to her incredible beauty, it was understandable that his lust and love for her overlapped. But all his fantasies about her remained just fantasies, since he knew that he didn't have the courage to act on them. He was still as shy about sexual matters as ever, so he didn't even try to flirt with her. She was his mother, after all, and he knew she wouldn't put up with that.

That pivotal overheard conversation had come just after Nick's sophomore year in high school. All through the following summer, he tried to think up ways to "offer his services" to help Margaret with her sexual problem, but none of the ideas seemed viable to him. The risk of failure was great, because it could hurt their loving relationship. At times, he even fantasized about blackmailing her to overcome the incest objections he knew she'd have, but he loved her too much to do something like that in reality.

His mother Margaret was no Bible thumper, but she had firm religious and moral beliefs. There was just no way she'd agree to incest, no matter what the situation with her husband was. He'd pretty much resigned himself that his fantasies would remain fantasies forever.

Things for him seemed just as hopeless with Hillary. Although they had many classes together, she barely knew him. Even there, without incest and marriage vows as obstacles, he was so shy that he made no progress at all. He had no love life because, to him, it had to be Hillary and no other girl would do. Since they had no mutual friends, he didn't he didn't see her at all over the summer.

His pivotal inspiration came one day near the end of summer after his sophomore year. when he was watching a Seinfeld rerun. In the episode, Jerry Seinfeld's friend George managed to date a really hot woman, even though George was chubby, bald and not very sexually appealing. George did this by showing off a photograph of a sexy woman he claimed was his last girlfriend. Other gorgeous women assumed that there had to be a reason such a hot woman was dating him, although they didn't know exactly why, so they agreed to date him too.

Nick spent the last weeks of summer vacation refining his plan and gathering the courage to enact it.

— — —

Finally, one afternoon the week before the 2002 school year started in mid-September, he decided he was ready. He found his mother sitting and reading a book in the living room. She was wearing an ordinary blouse, but the top couple of buttons were undone, showing off miles of cleavage. He'd hidden his lust for her so well that she didn't worry much about dressing that way around him.

He sat down on a chair directly in front of her. "Hey, Ma. What's up? You have a minute?"

He was trying desperately to act casual, but he wasn't succeeding very well. It's a good thing I'm too nervous to have a boner, because she'd notice a bulge in my shorts for sure. Why does Ma have to be so fuckin' hot and stacked?! I have to keep my eyes up at her face. Up, up, up!

She could see how stressed out he was, so she just smiled kindly and said, "Sure, Son. What's on your mind?"

He looked down at the ground, both because he was nervous and to avoid looking at her cleavage. "Um. Well... You know about me and Hillary." By that, he meant that she knew all about his obsession with Hillary. Since she was his close friend and confidante, as well as his mother, he'd told her about his feelings for Hillary a long time ago, and he had asked for her advice about Hillary many times. She always encouraged him to be bolder, but he always found himself unable to do that.

Margaret smiled knowingly, glad to see her son was finally showing a more active interest in girls and trying to overcome his shyness. "I sure do. I'll bet you're thinking about school coming up, and seeing her there."

As Margaret already knew, both Nick and Hillary were switching from one public high school to another at the same time, when the new school year began. Both had been accepted into the same "Advanced Studies" extra-gifted program at a different school. Only those with an IQ above a certain level were eligible, and even then only about 20 students in total from a cluster of all the nearby high schools were accepted. The program was only for the last two years of high school, so they were both switching schools at the start of their junior year.

Nick said, "Yeah. You know I've never REALLY talked to her, beyond saying hello and that kind of thing. But when we start at the new school, I'm gonna be nearly the only person she knows by name, since we're making the same transfer at the same time. We'll have all the same classes, or nearly all the same classes. And we'll both be in the same gifted program, and those classes are especially small. We'll practically be thrown together!"

Margaret smiled. "Isn't that wonderful? That sounds like a great opportunity for you to get to know her better. I'll bet she'll even seek you out, wanting to talk to someone who remembers her old school and all the people there."

He replied, "I know! But I'm scared! Ma, I'm totally, totally scared! I mean, I think I can deal with talking to her. I've been getting more confident in talking to girls, finally. Well, at least somewhat. But I don't just want to talk to her, I want to... you know! Date her and stuff. That's the big problem. How am I going to make that leap? From friend to... you know... date." He shyly looked down at the floor.

"Nick, you're a handsome boy."

"I am NOT!" he protested. He knew he was smart, but his self-confidence was low when it came to looks. He glanced down at Margaret's boobs. Her clothes weren't especially revealing, but there was still no way for her to hide her natural endowments. Damn! I can totally see the shape of her nipples. I swear, it's like there's two basketballs in there! Ma is SO STACKED! And the rest of her is just as amazing!

He forced his eyes back up to hers.

She said, "You are handsome. Now, admittedly, you're no Tom Cruise, but who is? You're more than handsome enough. And I'm not just saying that because I'm your mother. I mean it." It was true; she did mean it - although the fact that she was his mother did color her opinion a fair amount.

She added, "You've told me before that she's dated some guys who you thought were not as attractive as you are."

"Yeah," he admitted, "but they had other stuff going for them. They're outgoing and cool and jocks, and things like that."

"You have LOTS of other stuff going for you! You're smart, nice, funny, g-"

He cut her off and looked back up in her eyes. "Ma, that's easy for you to say. You're my mother. I know she and I will have a lot in common, but that would only make us good FRIENDS! To be considered a potential date with a total babe like Hillary, I need to have some kind of sexual charisma or something. And you know I'm a zero in that area. That's the one bad thing about us both transferring from the same school - I wish I could have a clean slate with her, but she knows enough school scuttlebutt to know that I'm a complete virgin who's never dated anybody, ever! I don't even know how to flirt! I'm hopeless! I'm a ZERO!"

"You're not a zero, Son; really you're not."

His eyes drifted down to Margaret's big breasts again, but then he caught himself and looked away. He complained, "You're just saying that because you're my mother. Encouraging words are nice, but they don't really help. I feel like a zero, so I have no confidence, and it shows! It's a vicious circle."

She knew there was a lot of truth in what he was saying, but she wanted to be encouraging. "Well, if there's anything I can do, you know I'd do anything to help you."

Those were the magic words he'd been waiting for. He looked up into her eyes again. This was the big moment to try out his plan. His palms were sweaty and his heart was pounding. "Really? You mean it? You're not just saying that?"

"Of course I mean it! I'm your mother! I'd leap in front of a train to save you. That's what caring mothers do."

He tried not to hide his delight that she was playing right into his hands with that comment. "Huh. Well, since you say that, there is one thing you can do that would totally help me out. In fact, this one little thing could completely change my life!"

She looked at him warily. She knew he was very clever for his age, and could be too clever for his own good sometimes. "Well, I'm willing to help, but within reason. What is it?"

He looked at her face more confidently now, gathering courage to make his appeal. "Ma, I've noticed something about women. Why do women like a certain guy? In my opinion, looks aren't as important for women as they are for men. I mean, with a gorgeous woman, just about every single guy is gonna be drooling all over her, even if she has the personality of a potted plant. But sometimes I see a good looking woman out with a not-so-good looking guy, and I wonder, 'What's up with that? What's he got that I haven't got?' You know what I mean?"

She corrected, "'What does he have that I don't have,' you mean. But yes, I've seen that kind of thing sometimes."

He went on with the appeal he'd prepared in advance. "Right. It's occurred to me that women, maybe more than men, take their lead from what other women say about guys. 'Is he good in bed? Is he well mannered? Is he a cheap date? Is he, well, you know, endowed down below? Is he a nice guy? Does he have a nice car?' And on and on. With guys, at least guys my age, all we think about is, 'Is she sexy?' We're pretty simple on this stuff, like cavemen or something. But girls, they think about all kinds of different things. They talk and talk and talk about guy stuff with their friends. Us guys, we don't really share any info, except when guys want to boast about their sexual conquests and stuff, and most of the time they're lying."

"That's all true, I suppose," she agreed. "That's how it was when I was your age, and I imagine it hasn't changed much. So what's your point?"

"I'm getting to that. At this new school, nobody's gonna know me from Adam, right? Except Hillary and a couple others I barely know who are also transferring from our old school, that is. So this is my chance to start a whole new reputation. I can instantly go from 'shy, lame virgin' to 'super studly guy' if I play my cards right. Even with Hillary, she'll think I've changed over the summer, since she hasn't seen me for a few months. I just need one thing to change everyone's opinion of me."

"What's that?" she asked, intrigued.

"A really, really hot girlfriend! Or at least a really hot pretend girlfriend. In other words, you!" This was the idea he'd gotten from the Seinfeld show.

"ME?!" She was surprised and incredulous.

"You!" He was so nervous he thought he would faint. It was a relief to get that much out, but the really big moment would be her response.

She protested, "Now wait a minute!"

"No, wait, Ma. Listen! I've figured it all out. It would be totally pretend. Obviously!" He laughed nervously. "All you'd have to do is show up after school and pick me up in your car a couple of times. Kiss me on the cheek and kind of act, well, like a girlfriend. Like you're all happy to see me and stuff. Then the other kids will ask me, 'Hey, Nick, who's that totally hot babe who picked you up from school yesterday?' And I'll say, all casual-like, 'Oh, she's my girlfriend. I met her this summer.'"

Her surprise turned to amusement. "'Totally hot babe?' Who's that?"

"Ma, that's you! Seriously! I know you're really modest and all, but you're seriously one of the most gorgeous women on the entire planet!"

"Oh, please!" She was enjoying the flattery. She found his compliment harmless and amusing, so she didn't worry about it too much. She knew he ogled her sometimes, but she didn't imagine that her sexually shy boy would want to act on his urges.

He said excitedly, "No, I mean it! You know what Hillary looks like, and how I think she's a totally hot babe? Well, I think you actually look even better and sexier than she does! If you weren't my mother, I'd be like... drooling! So what I figure is, Hillary will see you, see how beautiful you are, and think, 'Hey, if Nick is dating the likes of her, then he must really be a catch.' Meanwhile, I'll be her friend in class and stuff. Then, after a couple of weeks of you picking me up and dropping me off and whatnot, everyone will be convinced we're going out. At that point, we can pretend to break up. Then I'll wait a week or two, pretend to be all sad, and then I'll ask Hillary out! She'll say yes! She'll HAVE to say yes, if only to figure out how and why I could have been dating the likes of you."

Margaret laughed. "You've really thought it all out, haven't you?"

But to herself she thought, Actually, as crazy as it sounds, something like that might work. At the very least, Hillary would have to feel intrigued. Besides, it would be good for him to boost his reputation in general. The big problem is, I'm too old; I could never pass for a teenager.

He was excited and encouraged, since she didn't shoot him down straight away. "I have! Come on, Ma! Admit it, the idea makes sense! It could work! It WILL work, 'cos it'll give me the confidence I've been lacking. I've been doing some reading on how guys are successful with girls. The main thing is that confidence is everything! Besides, it'll not only help me with Hillary, it'll cement my reputation at school for years! I won't be seen as the sexually clueless uber-virgin going to the super-geeky Advanced Studies program. Instead, from day one, kids will know me as the guy with the hottest girl in the history of, well, ever!"

She laughed. "You flatter me, but seriously, I'm not all that. I'm not even half that. Nobody gives me a second look anymore. Besides, I'm your mother! I'm twice your age. I'm ancient!"

"HA! Ma, you're soooo not ancient. I know the way you and Dad had me wasn't exactly a fairy tale. You got pregnant with me when you were 15 and had a shotgun wedding at 16. I know that dashed a lot of dreams for you and stuff."

She cut in, "But it gave me new dreams, new happiness. Don't ever think you were a mistake. If I could do it all over again, I would, because if it happened any other way, I wouldn't have you."

"Awww, Ma, that's sweet. But still, my point is, we can find a silver lining to your early pregnancy. You're barely over 30-"

She snorted with derision. "Barely? Ha!"

"It's true! You are. You're so young. You're way younger than the mothers of any of my friends. But the main thing is, you look even younger than that. You always get carded wherever you go. You know it's true! You have one of those perpetually young faces. That's a fact. You wouldn't even have to try to look like a teenager, 'cos you look that way naturally."

She conceded, "Okay, so I still get carded sometimes. Big whoop. That doesn't turn me into a high school junior or senior all of a sudden. Teenager? Puh-lease! There's no way we could get away with that."

"Ah, but I've worked that out. We'll just say you go to the local university. You could even have been going there a couple of years. Will people believe you're a 20- or 21-year-old college student? Totally! You know I'm right!"

She considered that. "Okay, maybe you're right about that part. Maaaaybe. But that just brings up another problem. I don't mean to sound harsh, Sport, but if I'm this supposedly 'totally hot babe' a couple of years older than you and going to college, then what the heck would I be doing dating you, a mere high school student?"

("Sport" was her occasional loving nickname for him, one that only she used. She also called him "Son" more often. But he didn't have any special nickname for her since he always called her "Ma.")

He replied, "That's the whole point! It's intriguing. What IS this guy doing dating her? There must be something special about him!"

She laughed. "Touché. But it has to be at least somewhat plausible."

"Hey, it happens more often than you'd think. Admittedly, it's usually the other way around, with the male college student dating a high school girl, but why can't it happen both ways? Besides, I've worked out a background story in my mind. We'll say that you're boarding at my house. We'll pretend our family has rented out the bungalow in the back yard. You did badly in the housing lottery to get into the college dorms, so you're renting a cheap place off campus, and you're living back there in the bungalow. With you and me living just a few feet from each other, we naturally began to hang out, sparks started to fly, and the rest was history."

She thought, Damn! He's really thought this out. He's too clever for his own good. That would at least be believable enough for most people. I can't let this actually happen! What if I have to kiss him? On the lips, even! The whole thing could get really weird.

She held up a hand. "Hold on. For starters, that bungalow is really just a glorified storage shed. It's stuffed to the gills with old crap. Nobody could live there."

"I know that, you know that, Pa knows that, but nobody else knows that. It looks pretty big from the outside. Remember, the sum total of our so-called relationship would be you dropping me off at school and picking me up. We just need a plausible cover story for the rest. Nobody at school knows what you look like, not even Hillary. By luck, I've been biking to and from school every day for years and I never have friends over, so nobody would recognize you, not even kids from my old school. This is a case where my reputation for shyness and lack of friends actually comes in handy."

She pondered that. "True. But I did go to some parent-teacher functions."

"Yeah, but that was at the old school. This is a brand new school for me! We're totally starting fresh!"

She thought up a good point. "A-ha! But this will ruin things for the future. What if I want to go to parent-teacher meetings at the new school? Or you have friends over here next year, or the year after that, and they see me? Think of the implications. Nice try, but no cigar."

He countered, "I've thought that through. Sure, there could be a few difficult moments, but it'll be worth it. We can have you change your appearance so people won't recognize you later. Dye your hair blonde or red for the next couple of weeks. Or wear a wig, maybe. Wear flashy clothes, lipstick, dark sunglasses - stuff like that. Take a new name. One thing that's so totally perfect is that you've kept your maiden name of Palmer, so your last name is different than mine. It would work. Margaret Palmer has nothing to do with Nick Stevens. It totally would work!"

She shook her head. She found herself strangely excited, because this sounded like a mad adventure that would put some spice in her otherwise boring life. But she told herself not to encourage him. "No, it wouldn't. There are all sorts of problems. What if someone did figure out who I really am? We'd be in big, big trouble!"

He pressed, "But how would that happen if you dye your hair and such? It's not like you'd be talking to people, or seeing them up close. You'll just be dropping me off and picking me up."

She shook her head some more. "Sport, this is crazy. There's just no way-"

He put on his best sad-puppy-dog look. "Ma, didn't you mean it when you said you'd do anything to help me? This could totally change my life! Reputation is everything, especially at my age. This is THE key chance for me to reinvent myself. Do this for a couple of weeks and I'll seriously be able to ride this reputation boost for the rest of high school. And you could totally hype me up too. You know, hint that I'm a great lover and stuff like that. Even if things don't work out with Hillary, this could at least give me a dating life with some nice girl."

"Now, just a minute. Who would I be hinting to? You just said I wouldn't be talking to people. I'm just dropping you off, waving good-bye, a kiss on the cheek and that's it, right? Now I'm talking to other girls?"

"Well, you don't have to if you don't want to. Honestly, I don't know what'll happen. You know how Hillary is, from all the things I told you about her. She's not shy. What would stop her from talking with me after school until you come to pick me up? Then she might want to talk to you and ask you a few questions. That might happen once or twice - who knows? So we'd need to roll with the punches. But just think about it: that means I'd be walking with her, and talking with her! Wouldn't that be AWESOME?! Plus, that would give you a chance to meet her. Wouldn't you want to actually meet her after hearing so much about her?"

She chuckled. "Yeah, it would be nice to meet her. But... Hey, wait a minute. You're talking as if we'd actually do this. I hate to break it to you, but it's not gonna happen. No way." She defiantly crossed her arms below her big breasts.

"Why not? You said you'd jump in front a train to save me, but you wouldn't do this?"

She frowned. "Please don't throw my words back at me like that. I also said I'd be willing to help 'within reason,' and this is a little too crazy for me. You know I'd help you if I could. But this idea just couldn't work. So many things could go wrong. For one thing, what if it spiraled out of control?"

"What do you mean?"

"What if your friends don't believe that I'm really your girlfriend? After all, it would be a stretch, if only because of the high school - college difference. And I don't believe for a second that I'm this great hottie you claim I am, even though some people do tell me I'm attractive-"

He interrupted, "Oh, come on, Ma. You're a total babe!" Normally, shy Nick would never have told her something that bold, but his confidence was growing the more they talked about his plan.

He said, "The thing is, you dress like a plain Jane and hide behind dark sunglasses. It's like you don't want to be noticed. Especially since your de facto break up with Andy, you've been keeping a very low profile. Half the time, you go out wearing the kind of clothes you might want to use when painting the side of a house. Believe me, if you allow your beauty to shine through, everyone will see you're a serious hottie."

She blushed a little at that. "Never mind that. What if they demand proof? What then? What if they expect to see you kiss me on the lips?"

He shrugged. "Big deal. So we'll kiss on the lips. We can just keep our lips closed and fake it. Heck, your cousin Hildy kisses me on the lips at family reunions. It's no biggie. We just have to roll with the punches. If things get out of hand, then we'll just break up." He made quote marks in the air as he said "break up."

He was trying to act nonchalant about the problems she mentioned, but he was secretly delighted by the prospect of the plan spinning out of control. In fact, that was his greatest hope.

The way he looked at it, the plan could serve two purposes. His main goal was to use the fake girlfriend idea to kick-start a physical relationship with Hillary. He felt it honestly had a good chance of success. But on top of that it would give him a chance to spend time with his mother in at least a semi-romantic setting. Even if their romance was just pretend on her part, it would still be a thrill for him. For instance, he remembered how much he'd envied the boy who got to play opposite Hillary in the school play the previous year, and that was just an acting role. If all he got was to kiss his mother on the lips a few times, that would still make all the effort worthwhile, even if they were fake kisses.

Aside from that, he was mostly being honest about his goals. He did think his scheme might do wonders for his reputation at the new school, even if it didn't have any effect on Hillary, so he might at least be able to date somebody.

He figured the odds of this working well enough for him to get sexually intimate with his mother were like a remote moonshot. But as long as there was any chance whatsoever of that happening, his life would be a lot more exciting.

— — —

With only a week to go before the first day of school, Margaret still flatly rejected Nick's plan, but he badgered her about it relentlessly. They discussed it every single day - but always when his father wasn't around. Slowly but surely, Nick turned her around. She never flat-out agreed to do it, but they gradually went from arguing about doing it at all to arguing about the how-to-make-it-work details. When she bleached her hair blonde three days before school started, he finally knew for sure she'd go through with it.

Interestingly, they never did tell Andy about it. At one point, Margaret told Nick that Andy would be against it, but she figured that what her husband didn't know about this "harmless prank" wouldn't hurt him. Andy couldn't help but notice the change in her hair color and style. So she told him that she'd impulsively dyed her hair and changed her hairstyle while at the beauty parlor one day when she realized how bored she was with having her hair exactly the same, year after year.

Actually, she looked incredible with her new hair color. Before, she'd had a kind of mousy light-brown hair that was one of her least attractive features. The blonde color looked perfectly natural, as in fact it wasn't that big a change from her normal hair color. But the blonde hair caused more people to give her a second look and then see just how attractive her face and the rest of her were. After a couple of days going out for errands showing off her new hair color as well as her new hair-do, she couldn't continue to deny to Nick that she was still a real head-turner. She was starting to come out of the self-imposed isolation that had started when her marriage fell apart.

Nick could hardly wait for the big first day at his new school. Normally, he dreaded the end of summer and school starting. He hadn't really been considered a "true" nerd since he was unusually good at school sports, but he generally kept to himself and didn't have many friends. He was more of a loner than a nerd, since he didn't even hang out with the other nerds much. Partly that was because he was shy, but partly it was because he didn't relate well to kids his own age. They seemed immature to him, and his taste in music, movies, books, and so on was different from just about all of his classmates.

Normally he would have had a particular dread at the prospect of talking to Hillary face to face. Now, thanks to his fake girlfriend scheme, he was actually looking forward to it. If nothing else, his plan was already a big success in that it had boosted his own confidence a great deal.

He had always feared Hillary might reject him, despite the fact that she always seemed sweet and nice even to guys who were socially clueless with her. She was a naturally nice person who knew how to let guys down gently. But he didn't fear her rejection much anymore, because he felt he had an 'ace in the hole' that was an almost certain guarantee of success.

Of course, there were a lot of big 'what-ifs,' but he was very hopeful she would at the least start to see him as potential boyfriend material after she saw him with his hot "college girlfriend." That was vital, because the thing he dreaded most of all was having Hillary take pity on him, humoring him as he flailed about while trying to talk to her. Once she thought Margaret was his girlfriend, even if she did turn him down, he could act like he didn't mind at all since he could do as well or better. Margaret would be the proof.

As the first day of school approached, Margaret's attitude started to improve. Nick was ecstatic that she was obviously starting to get enthused about the whole idea. She relished the opportunity to dress up and have some fun. Because of Andy's accident, Andy's resultant reluctance to leave the house except when absolutely necessary due to his damaged legs (and only if Margaret drove him), and the fact they didn't get along anymore, Margaret hadn't had many chances to really dress up in the last two years.

This was a chance for her to turn back the clock and be seen as the "totally hot college babe" that she'd never had the chance to be. Because she'd gotten pregnant so young, she'd missed out on many aspects of high school life, and she'd had no possibility of going to college. So she began looking forward to having a second chance to act like she was that age again, even if only for a little while.

She actually bought a whole bunch of stylish new clothes, together with some killer Matrix-styled dark sunglasses. She'd even bought some sexy bras and panties. She assumed no one would see them but herself, but she felt they would help her assume a sexier attitude. She drove a red, five-seat Toyota Prius, and while it wouldn't be as hot as showing up in a fancy sports car, it was still only a year old and looked really good. She even took it to the car wash and got it cleaned inside and out.

Nick could hardly wait for the first day of school. Over the previous week, he'd masturbated more frequently than he'd ever done before, just thinking about all the things that might soon happen. If his wildest dreams came true, he might have at least some sexual success with both of his obsessions!

NOTE: Thanks to the suggestions and corrections of YamiBoy, Ecchi Spud, markgr, GWB, BDGV, and Johnny Galt.