Kinda-Sorta-Maybe Nerd-Boy - Cover

Kinda-Sorta-Maybe Nerd-Boy

Copyright© 2007 by bluedragon

Chapter 1: Miss Popular

Erotica Sex Story: Chapter 1: Miss Popular - A teenage nerd-boy spends the next few years on a mission to become popular and find his dream girl. This is the story of his success... sort of...

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Teenagers   Consensual   Group Sex   First   Oral Sex   Anal Sex   School  

HIGH SCHOOL, FRESHMAN YEAR

Dude, reality bites.

The utopian world of my imagination was soooo much better than this. In my imagination, everything made a logical, mathematical kind of sense. I envisioned a human race where the fact that I was a foot shorter than most of the boys at school was not an insurmountable obstacle. In my universe, intelligence was rewarded with respect from one's peers, not free trips to the bottom of the nearest trash can, courteousy of the local football jock. I swear I still had someone's old yogurt in my hair.

It was only the first day of school, and two trash cans later I had decided to commit seppuku, or some other archaic form of suicide, as soon as I got home. My backpack must have weighed more than I did, and I could feel my spine bending out of shape already. I would look like Quasimodo by the end of the school term.

I missed my old school already. I had always lived nearby to the local public schools, but my parents had put me through a private school during my formative years. It was only now, in High School, that my dad had seen fit to move me to a public school. It would build character and give me a chance to develop my social skills, he had said.

He never told me exactly HOW I would develop social skills, however. I had a bowl-haircut because my mom thought it a waste of money to take me to a hairdresser when she could do the job herself. My glasses were big, fat, and hideous. I wasn't an ugly kid, by any means. But given a start like that, I might as well actually BE as disfigured as Quasimodo, too.

I sat on a bench by the parking lot, my feet swinging in the air as they did not quite reach the ground. I waited for my carpool classmates and my mom's minivan to arrive, my hyperactive mind already finding new things to occupy itself. Plotting out the most minute detail in my head, I believed that I had found the proper technique for killing myself. But that's when she walked by.

Glittering, bright blue eyes. Silky, shimmering dark hair. Elfin, dainty face. Perfect smile filled with rows of pearly-white teeth. I'd like to say that these were the first things I noticed about her, but they weren't.

To be certain, she possessed all of these amazing attributes, but my eyes had glued onto her FABULOUS breasts.

I wasn't familiar enough with girls to determine cup size, but they seemed pretty damn big on her petite frame. She wore some tight, quarter-sleeved top with a scooped neck to show off those round, perky globes of heaven that gave every male within a hundred yards an instant woody. And as my vision expanded to the people she was with, I nearly passed out from sensory overload. She was walking with a group of upperclassmen cheerleaders, decked out from head to toe in perky school colors. Well, head to ass, I guess, since their skirts really didn't go down very far.

My mouth dropped open, thoughts of suicide quickly vanishing from my mind as I realized my purpose in life. How could I even think of leaving this world when such heavenly creatures attended my school?

Oh, did I mention that my previous private school had been all-male?

"Hey, Jason! Wake up!"

Crap. Was this nothing but a dream? Oh, but to stay asleep forever and dream such wonderful dreams, to have this angel with me for all eternity.

"Dude, you're gonna drool all over yourself."

"Huh?" I turned my head, tearing myself away from the vision before me. My best friend Marcus was waving his hands in front of my eyes, snapping his fingers to get me to come around.

"Man, one would think you'd never seen a girl before."

I looked back at her departing form, her skintight jeans hugging her every curve as she sashayed down the sidewalk, oblivious to my very existence. "That's no girl. She's all woman."

Marcus gaze followed my own. "That's Amanda. She was in a couple of my classes the last few years, but man did she grow up over the summer." His eyes gazing appreciatively at the females, he clapped me on the shoulder and said, "Welcome to public school."


The rest of my freshman year passed by relatively smoothly. Over time, the school bullies found new prey to pick on, although Todd Beckman did saran-wrap me to the flagpole in January.

As we all began to get involved in after school activities, the carpool was pushed back until 4PM every day. I was part of Math and Chess clubs half the days of the week. The other days I found myself gravitating to the basketball courts where most of the other students played pick-up games. I was a late bloomer, and thus a tad underdeveloped (I was vertically-challenged) so I never got to play. But watching the games was more exciting than sitting around doing nothing. I usually had my homework finished in fifteen minutes, so I otherwise had almost two hours of time to kill.

Marcus, on the other hand, was in the exact same clubs as I was, but had hit his growth spurt a bit early for his age. He was as tall as many of the seniors in the school, albeit a skinny and gangly kind of tall. But his height had led to his inclusion in the basketball games, where he proved he at least had some minimal coordination. His full name was Marcus Yao, and he was Chinese, the tallest Chinese the upperclassmen knew. They all just called him "Yao" since it was more fun to say than "Marcus", and they kidded around that someday he'd be a big NBA star.

The third and final member of our carpool was my next-door neighbor, Kendra. Her dad was an immigrant Japanese businessman who found the stereotypically perfect woman to marry, a six-foot tall white woman with beach blonde hair. Kendra had inherited her mom's athleticism and was always in the pick-up basketball games as well. She even played on the girls' Junior Varsity team. As it was, she was a total tomboy, spurning makeup like it was a deadly toxin and dressing in loosely-fitting athletic apparel to hide her figure.

At 3:55 I would be the first one to our carpool location. At 3:59 I would open the doors and wait for the two basketball junkies to get loaded in before I jumped in. My mom taught me to be courteous and chivalrous, although Kendra resented me doing anything special for her "because she was a girl."

Marcus had been my best friend since before time, playing video games and card games and watching Star Trek reruns. Kendra I had been acquainted with, but since I was a kid who never went outside (except to go to school) I never got to know her before. But on our repeated journeys to and from school with nothing to do, Marcus and I found Kendra's inner nerd and we began to develop a comfortable friendship.


By sophomore year the three of us were firmly entrenched in the Nerd cliques. Kendra wasn't completely out of place; we had several female friends who similarly despised anything considered too "girly." By this year I had finally grown up, and had also joined the after-school basketball kids, and found that our little trio had become "orbitals" around the two social groups. On half of the days, we went to Math club and Chess club and did generally nerdy things. The other half we played ball and I was developing a solid 3-point jumper. We were freely accepted in both groups, while not being part of the inner circle of either clique.

Maybe this is what my dad meant when he spoke of learning to socialize. I had considered myself forever destined to be a nerd, but I started to believe that I was a decent social creature. Compared the rest of the nerd group, our trio was pretty popular.

Of course, this little ego-balloon was about to be crushed. I was about to find out just how much farther I had to go to be "popular." My life completely changed second semester. It was biology class, and the teacher assigned us lab partners. When I walked up to the posting outside his office and saw the assignments, my jaw dropped to the floor. My lab partner was Amanda.

To be sure, I knew perfectly well that she was in the class. A girl like that was impossible not to notice. But I never expected to have any actual face-to- face contact with her. Then I smelled a sweet floral perfume next to me, and felt an accidental bump to my side as someone jostled for position to see the assignment sheet in front of us.

Now in my defense, the natural position for my head is always slightly tilted downwards. I never really stand up straight, partly because I want to watch the ground where I'm going and partly because I don't have the self-confidence to walk upright. So when I turned around the first thing my eyes latched onto was Amanda's perfect cleavage a few inches away from me.

She reached her hand out and placed a finger under my jaw, lifting up to click my gaping mouth shut and then pushing higher to get my eyes to meet hers. Dropping her hand, she just smiled at me and asked, "You're Jason, right? I guess we're going to be partners!"

She suggested that we either meet at my place or at school after class for homework purposes, explaining that her home wasn't suitable for studying. The last thing I wanted to do was show my complete model collection of every Starship Enterprise to the prettiest girl in school, so I readily agreed to meet after classes. Things luckily worked around my clubs' schedules. I would have to miss a basketball game here and there, but I couldn't think of a better (or more frightening) way to spend those afternoons than with her.

Amanda turned out to be a very smart girl, but she wasn't above letting me do all the work. But you know, I didn't mind being used. I just enjoyed every minute I had in her presence. She was a natural conversationalist and flirt, with the innate ability to make me feel like I was an important person to her. Senior jocks would pass by when we were studying at the library, trying to hit on her right and left. Amanda just blew them off, getting a little angry at them for interrupting our study time and calling them 'stupid Neanderthals'. She was too good to end up with a brainless gorilla; she deserved a man of intelligence. I half-believed that she shooed them away so she could be alone with me.

Whenever we passed in the hallways, she would always smile and say hello to me. My heart fluttered every time she did that, to the point where I memorized her class schedule so I could be strategically placed outside her classroom door so we would bump into one another. Yeah, it's a little creepy, but I was a kid with a hopeless crush.

Marcus and Kendra continually teased me about her, asking when the wedding was going to be and trying to find out how many kids I wanted to have. I told them to screw off, and would always challenge them with some video game to get them to stop bugging me about her.


By junior year I had grown another inch and started up a job on the weekends. The first things I did with my earnings were getting a new haircut and buying a set of contacts. Meanwhile, I had always been blessed with a good metabolism, and after Kendra's mom bought a set of weightlifting equipment, our trio messed around "lifting" often enough that my body at least took on a decent level of definition. I was no Adonis mind you, but at least I was light years beyond Quasimodo.

I would still bump into Amanda here and there, as we had two classes together this year. She complimented me on my new appearance, and even started to give me tips on updating my wardrobe. I would overhear her friends commenting about me and saying that I was kind of a nerd, but my heart leaped as she always defended me, saying that I was "really sweet."

Meanwhile, my two best friends were also starting to grow up a bit. Marcus got his license and his parents bought him a beat-up sedan. Kendra's and my parents paid his gas so that Marcus could continue our carpool. Kendra had even started to wear a bit of makeup, and every so often would swoon over Brad Pitt and Will Smith, while Marcus and I would counter by drooling over Denise Richards and Jennifer Love Hewitt. And as much as I hated to admit it, Kendra was growing a pair of breasts. Always kind of weird to think of one of your best friends in that way.

The three of us also found ourselves growing apart from our nerd clique as we got involved in more social activities in school. In a way, I felt like we were still nerds in a sense, but we all shared an unspoken ambition to not be nerds anymore. The lure of popularity had hit us, through basketball, non-nerd friends, and the sexual attraction to the opposite sex. It was the thing every High School kid desired above all else, even if we tried to deny it.

We were hanging out with a "cooler" crowd this year, although not quite at the lofty level of the football jocks and the cheerleaders, but several steps up from the nerds and the stoners. Amanda even talked to me more often this year, albeit usually to get some help for homework or to prep for the upcoming exam.

In April we had our Junior Prom. One day, I summoned up all of my courage and approached Amanda outside her classroom. "Hey, Amanda."

"Hi, Jason! How are you?"

"I'm great. I'm great. Uh, I was wondering, uh. You know the Junior Prom is coming up and, uh, well I was thinking that, uh, if you're not already going with anyone then, uh, well, I mean, if you need a date, then, uh..."

She shushed me with a finger to my lips. She grinned, and then tapped the tip of her finger on my nose. "You're cute."

And with a radiant smile, she was gone.


By senior year Marcus, Kendra, and I had bumped ourselves up to higher levels of "popularity" in the school. Marcus and I kept working out until we had trim, athletic bodies. A part of me missed spending that time on Star Trek and video games, but this all-encompassing drive to be popular weighed on us heavily. Kendra had made the Varsity team in both basketball and volleyball, and was something of a school celebrity when she made the game winning shot against our cross-town rival. But the big event that kicked us in the direction of popularity came towards the end of first semester. I was eating lunch with Marcus and Kendra when Amanda came up to me, her perfect teeth dazzling as she smiled at me.

"Hi, Jason! Hey, guys! How are you doing?"

We chit-chatted aimlessly. I could tell the three of us were practicing the art of the small talk while simultaneously working to avoid sticking our foot in our collective mouths. After an appropriate small talk period, Amanda explained that one of the jock's parents was out of town for the whole weekend, and he was throwing a party. All of us were invited, actually. I agreed without looking to my friends for confirmation, anxious for any chance to be near this girl.

The night of the party came, and the three of us immediately felt out of place. So much for having graduated beyond nerd-dom. Compared to the reveling teenagers, we were amateurs among the socialites. Our insecurities and self- consciousness threatened to overwhelm us into muteness.

Well, nothing a little alcohol couldn't cure.

Three shots of tequila later, Marcus was an animal, diving into the backyard pool with all of his clothes on, quickly followed by six other drunken kids. Kendra got quickly plastered and was dancing in the living room with the rest of the crowd. She was more girly and more sexual than I had ever seen her before, her hips grinding erotically to the music as she freaked with the very type of dumb gorilla she usually despised.

I got plastered myself, and while dancing a few feet away from Kendra, I felt like I was seeing her for the first time. Her hair had come loose of its usual ponytail, cascading in a silky wave to frame what I had never realized was a very pretty face. Time and her mom's genes had been kind to her, and her budding breasts were doing a very good job of filling out her bra. Add that on top of her athletically toned body from her basketball and volleyball workouts, and I was beginning to realize that Kendra was a beautiful girl.

She smiled at me, and smiling back, I began to shake my body over towards her. I felt a compliment at the tip of my tongue for her, and for a moment she was the only girl in my universe.

And then my nostrils flared as I scented an all too familiar perfume, and then Amanda was in front of me, sliding a fresh plastic cup of beer into my hand while downing one of her own.

She hiccupped, and grinning at me, shouted a little too loud. "Glad you could come!"

I just smiled back at her, and then made a move to take a swig from my drink.

Apparently forgetting that she had just given it to me, she stopped my hand and pulled my drink away, setting it on a table against the wall. "Drink later. Dance now!"

I was only too happy to oblige. Amanda wore a paper-thin silk camisole that did nothing to contain her bounteous bosom, which bounced and jiggled with her every movement. Her hair was held up to show off a graceful neck and dangling silver earrings, with black miniskirt and high heels to complete the perfect picture. Her eyes bored into mine as we danced together, and when the music changed to something with a slow, solid bass beat she moved in close, until her whole body was rubbing against mine.

Her hand was on my chest, her eyes losing focus every now and again while she stared into my face. Her hips ground against mine, the erotic dance filling my mind with images of what it would be like to have sex with this goddess. My hand had wandered below her waist, and had settled onto a firm ass-cheek. She made no attempt to remove my hand, but only ground herself into me further, her eyes lifting up to capture mine once again.

When the song ended, Amanda complained that her head hurt and she wanted to take a break. I released her, but when she turned to move off the dance floor she took my hand in hers and tugged me after her. Without resistance, I followed wherever she led me.

We went up the stairs, and Amanda muttered that she wanted to lie down. Her movements were anything but fluid by now, and she seemed to have trouble maintaining her balance. I did my best to support her, and every few steps she would collapse against my chest, her arms around my neck. She popped open one of the bedrooms, but I quickly shut the door and backed us out into the hallway once I realized it was already occupied.

Now I'd seen a porn video a time or two with Marcus and Kendra when our parents were out. But I'd never seen a sex act live with my own eyes. A senior cheerleader I recognized was flat on her back getting her pussy drilled by a jock's fat dick, and I felt a flash of arousal stirring past the alcohol in my system. But then I managed to get the door closed, and fought to get my heartbeat under control.

At the next bedroom I knocked first, and when no answer came I cracked the door open and sighed in relief that it was unoccupied. I lifted Amanda into my arms, and then gently lay her down onto the bed. I sat next to her, a tender gaze across this angel half-asleep next to me.

For a moment my mind flashed back to the erotic dancing we had been doing just a few minutes earlier, and to the... fucking... I had witness moments ago. My sight returned to Amanda, lying flat on her back with her legs spread wide, and I felt the blood rushing out of my head and into another appendage as my hyperactive imagination ran wild.

I felt the caress of a hand in my crotch, and I looked down to see Amanda's eyes closed, with a contented smile at what she found between my legs.

Now I knew I was letting my imagination run a little too wild, and I shook my head to clear the cobwebs of alcohol and fantasy from my head. Only in my wildest dreams.

But when her hand dipped underneath my cargo pants, and I felt a cool hand wrapping around my shaft, my eyes bugged out with the realization that this was no dream.

"My, my. You've been hiding a monster inside of here all these years!" Amanda's eyes were wide open now, if a little bleary, and she unzipped me to give her hand freer access to my rock-hard shaft. With her other hand, she pushed me down until I was lying next to her on the bed, then she sat up and straddled me, her hand still down and firmly pumping my rod.

She leaned down and kissed me, and all that was left of logical and rational thought left my mind. If this was only a fantasy, then I was going to dive in and enjoy it. Her tongue trailed out along my lips before darting back in to dance with my own. I had nothing to compare it to, but Amanda was a great kisser.

My arms automatically encircled her, rubbing and caressing her back. I slipped one hand beneath the back of her camisole, stroking her spine. She moaned into my mouth before sitting upright, whipping off her top and then unsnapping her bra.

Those fabulous orbs I had only ever dreamed of spilled out to my hungry gaze, firm and skin tight as drums stretched across perfectly shaped melons ripe with mingled perfume and sweat. Her dainty nipples were turgidly poking out at me, calling me to them. And she leaned down to feed her tits to me, gasping little sighs of pleasure as I instinctively began to suckle. This was heaven.

And it of course had to end. I could feel my dick starting to spasm, and I would lose all control in another minute. My body tensed as it prepared to spew my load all over her hand and my stomach, but then the door burst open and a red- headed cheerleader poked her head in. Her gaze swept across Amanda first, but then her smile vanished when she saw me.

Amanda dismounted me onto the bed, embarrassed for the moment and hiding her tits from the football jock now peering through the open doorway. The red-head looked down to my twitching member, and whistled her appreciation. "Now I know why you like him so much."

Then the red-head pulled the door tightly closed, and we were alone once again. Amanda just giggled and gave me a "sorry about that" look. The moment was gone, the magic broken. She reached over to pull her clothes back on. I ogled her very obviously until heaven was removed from my view, and I stuffed my painfully hard meat back into my pants.

If nothing else, the events of the past half hour had sobered us both up a bit, and Amanda declared that we needed new drinks.


After a few minutes Amanda left to chat up some other friends, and I went to find Marcus and Kendra. Marcus had driven to the party, but he was in no condition to drive us back. Neither was Kendra for that matter. I gave myself another half an hour to make sure I was clear headed, and then loaded my friends into Marcus's car to get us home. I dropped off Marcus, explaining he could pick up his car tomorrow. He staggered into his house, carrying his wet shirt with a "borrowed" towel wrapped around his upper body.

Kendra was a slightly more complicated problem. She was so far gone she was practically unconscious. I parked the car on the street outside our houses, but she had neither the strength nor the awareness to stand up on her own. So I settled for scooping her up into my arms and carrying her up to her house. With her arms about my neck, she pillowed her head on my shoulder, mumbling against my neck which was simultaneously tickling and a little pleasurable.

I had to fish her keys out of her pockets, and for a moment felt a little weird with my hand caressing her hips, albeit with honest intentions. As quietly as I could, so as not to wake her parents, I carried Kendra upstairs to her bedroom.

She seemed to wake up a bit when she realized she was home, and I laid her out across the bed. Exhausted from dancing all night, she merely slid herself underneath the covers without changing, then thought better of it and after a bit of squirming around under the comforter, dropped her skirt out onto the floor.

I knelt down on the floor next to her bed, absently reaching out to draw her hair away from her eyes and then stroked her cheek. "Did you have a good time tonight?"

"Yeah..." she breathed out. "Thanks for getting me home in one piece."

"Anytime."

For a moment our faces were just inches apart, her eyes luminous as they stared into mine. Then I got up and went home.

Later that night, as I sunk myself down into my bed, Kendra's sweet face came unbidden to my head. She looked so sweet and peaceful as she slept, and I felt relaxation pooling over me like a warm blanket. But then my memories flashed back to a strange bedroom and a topless Amanda in my arms. And I surrendered myself to a dream world that would return me back to the fantasies of my imagination.


Only a few months later, bids were going out for the Senior Prom. The High School was suddenly abuzz with the latest scuttlebutt and rumor about who was going with whom. And we surprisingly found ourselves in the middle of the rumor mill.

Ever since the house party our trio's stock in popularity had skyrocketed. Even though he didn't remember most of the night, guys had been coming up to Marcus for weeks crowing about how wild he was, and he found himself getting picked automatically at every after-school b-ball game. Kendra was fending off guys left and right, people whose names she didn't even know were trying to flirt with her and invite her to Prom. The rule went that it was better to go with a popular girl you didn't know than a less-popular girl that you did know.

After a few days of this Kendra dragged me off during a break between classes. "Jason, you have to save me from all these horny bastards. Will you take me to the Prom?"

Surprised, it took me a while to fumble for an answer. "Uh, aren't guys supposed to do the asking?"

"Oh, come on. You know I never cared about that male roles/female roles crap."

"Well, it's just that..." I looked over her shoulder, and my eyes found the woman I was looking for. "I was going to ask..."

Kendra turned her head around, seeing Amanda and her big, round, twins leading the way towards us in the middle of a crowd of fellow cheerleaders. Kendra turned back and grabbed my jaw, rotating my head around none too gently to bring my attention back to her.

"Jason, you are such an idiot. I know you've had a crush on her since Day 1 of High School but do you really think she's into you? She's the most popular girl in school and you are nothing compared to her. Don't tie yourself up in delusions of grandeur. I'm your friend. I just don't want to see you get hurt."

My mind rebelled at what she was saying. I was popular now, dammit. I'd worked hard at it. I'd skipped out on doing things that made me happy to do things that would help me socially, things that I needed in the long run. I'd smothered my geeky urges to play Dungeons and Dragons and Warcraft so that I could join the in-crowd. And dammit, I'd made it.

Kendra just looked deep into my eyes, her finger on my lips to forestall any further comment. "Jase, this is me. I know you. And as much as you want to deny it, you're still a geeky nerd-boy. Now that doesn't bother me, but a girl like that would never accept who you are. And is that really the kind of girl you want to be with?"

I took her fingers away from my lips. Amanda had been atop my pedestal for years. She was the one thing I always dreamed about and yearned for. Was that the girl I wanted to be with? "Hell, yeah."

And I walked past my friend, moving to join the gaggle of girls around Amanda. I did look back, just once. Kendra still had her back to me, but her head was turned towards me, and I saw a tear dribble down her cheek. Tomboy Kendra, who used to pride herself on being tough and free from "girly" emotions. It was the first time in four years I'd ever seen her cry, and it was almost enough to get me to stop.

But I turned back and saw Amanda's angelic face, and my heart hardened to what I had to do. Slowing down into the swagger of all the cool guys in school, I slid in and started to chat up the various girls. I maintained the conversation all the way down until we reached Amanda's classroom, where we stopped momentarily outside and I got her attention.

"Hey, I was wondering if you already had a date to Prom."

Her eyes glowed for a second, a happy smile tugging at the corner of her lips. My heart was thudding into my throat, but then I felt it fall into my stomach when her smile drooped into a frown. "Ah, well. I'd love to, Jason. But Tommy Beckman asked me this morning, and I kind of already said 'yes' to him."

Tommy Beckman. I still remembered the day his older brother saran-wrapped me to the flagpole. I fumbled for something to say, but the insecure geek in me rose up and turned anything I could say into a stuttering noise.

"Well, he's the star quarterback, and I'm the head cheerleader and it all just goes so well together. But hey, you can sit at our table and we can still hang out. Wouldn't that be fun?!"

Finally I managed to croak out, "Sure, that would be great."

"Okay then. See you later!" And she skipped into the classroom.

As I turned to watch her leave, I felt a very deliberate squeeze on my ass. Spinning around I saw the red-headed cheerleader from the house party sizing me up. "Hey there Jason. I'm Patrice."

"I know, I remember you." I didn't actually know her well, but I was playing along. Why was she talking to me right now?

"Well, I've had a few others ask me to the Prom, but I was saving myself for the right guy. You taken?"

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