My What If

My What If

by

warkat747

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Authors Note: This is a work of fiction. All the characters are fictitious figments of the author's imagination and are old enough to be doing what they do. All the places are fictitious fragments of the author's geography. And all the fictitious things that the fictitious people get up to in the fictitious places are most certainly nothing more than consenting fictitious filaments between the fictitious adults derived from the authors', probably non-fictitiously, disturbed mind. Enjoy.

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I noticed her immediately on the first day of the spring semester as I walked into the music room where students of all grades commingled. I didn't know who she was and wondered how I had never seen her before. She could best be described as petite. Short, thin, with a smooth curve at the hips, small breasts, straight ginger red hair down to just below her shoulders, freckles on her pale skin, and a little snub nose. Breathtaking.

I paid attention at roll call to find out who she was. Surprisingly, I recognized the very Irish last name and suspected I had known a younger sister of hers, who was in my grade, for years. They looked nothing alike. I went home and looked her up in the old yearbooks. She had been there the entire time. Ashleigh. How had our paths never crossed before?

I had no great interest in this music class, having only signed up for it as a girl I had known and fancied for ages was taking it. As it turns out, she and Ashleigh sat beside each other. That was convenient in a slightly awkward way, the girl I had been pining after for years and the one who had, at first sight, stolen my attention away from her within the same furtive glance. Not that either of them knew any of this.

The girl I had been after and I had met way back in Kindergarten, and I knew my chances of romantic interaction with her were zero. Fantasies aside, this lengthy association also meant I had no nervous hang-ups with her. We could converse at ease with none of the debilitating social stigmas that often exist in the hyper-gossipy blown out of all-proportion world that is a high school. And so it was easy to innocently ask her how music class was? Hey, who's that girl sitting next to you? Is she new? Oh, that's so-and-so's sister? I didn't know she had a sister. Gleaning whatever pathetic little bits of information I could from her without giving away that I was smitten by this redhead I had never met.

I continued to admire Ashleigh from afar, as was my way. I was much too shy to go and talk to her. Perhaps a month into the semester, I had just finished lunch and was leaning against a wall near the trash cans in the cafeteria, waiting to be released from the tyranny of the lunchroom back into the tyranny of the classroom, when the object of my desire suddenly appeared at my side.

"I think you're cute," she said.

"Excuse me?" I said like an idiot.

Two other girls, whom I had come to recognize as her friends, showed up, and Ashleigh walked off with them. I hurried to the music room to process what had just happened. People began to filter in, she among them. Instead of taking her seat, she walked over to where I was sitting and sat down on my left leg, her legs between my left and right legs, her right arm over my left shoulder, and her hand on the back of my chair. She was rocking her butt back and forth on my leg; whether this was for balance or if she was grinding against me, I wasn't sure. But I was hyper-aware of it.

"I think you're cute," she said again. She was looking right at me as she said it. She had grey eyes. I didn't know what to do. I noticed the girl I used to fancy looking at us through the corner of my eye.

"Did she put you up to this?" I nodded in her direction and expected to see her bust out laughing any second.

"No," she said, much to my surprise. "She told me all about you when I asked her who you were."

"You asked her about me?"

"Yep, MARCUS." She used my actual name, something I tried to avoid people knowing altogether, much preferring to go by Marc, proving that she had indeed talked about me with one of my oldest friends. She got up and walked back to her seat as class began. The next day, she sat on my legs again after lunch, but this time, she straddled them both, her legs outside mine. I was instantly hard as a rock. The stiffness of my denim jeans was the only thing keeping me from pitching an obvious tent in my pants. How I wished she would slide a little bit closer and grind her jean-clad pussy over my cock. I probably would have cum right there in the music room and not cared a bit.

As the weeks and months went on, we flirted back and forth in our pathetic, okay, in MY pathetic manner. We would end up standing next to each other in line, or if we had to take a bus someplace to perform, we might end up in the same seat. Wow, this bus is sure a bumpy ride, so it's not our fault we slid into each other around that corner. But really, nothing was happening outside of my fantasies and, with some luck, hers as well.

One day in early May, she asked me if I ever went to the stockcar races on Friday nights at the local fairgrounds. I told her I didn't. Only after I answered did I realize she might have been asking me to go with her. What an idiot I was. When Friday came around, all I wanted to do was go to the fairgrounds and try to spot her. I had access to a car but would have had to pay to drive it into the fairgrounds, and funds were scant at best. So it was onto my trusty bike, and then naturally, peddling my ass over to the fairgrounds at full speed.

The fairgrounds were at the eastern edge of town. The western perimeter was composed of half a dozen large buildings, massive industrial barns that housed various types of livestock, and displays from local vendors when the county fair was taking place. The racetrack, a clay oval, pit area, and the big grandstand were off on the north end. The southern and eastern part of the fairgrounds was a large 'L' shaped hill, its flanks wooded except for a large clear area used for sledding in winter. The town's water tower was perched at the hill's highest point, and the top and back sides were grassy and sloped down into farm fields. This left the center of the fairgrounds relatively flat and wide open to be used for carnival rides during the county fair and parking for the races.

I pedaled my sorry ass past the main gate and into the fairgrounds and, avoiding the endless stream of cars, maneuvered my way over towards the grandstand, desperately searching for a glimpse of ginger red hair. The grandstand was just a monolithic metal wall from the outside. The racetrack was hidden by a tall fence of corrugated steel plastered in advertisements. The crowd around the ticket booth and food vendor stalls made spotting a specific person almost impossible. I rode my bike back a fourth past all this a few times and didn't spot a trace of Ashleigh. It finally occurred to me that maybe she didn't even go to the races. If she was asking me out, a big if, perhaps this was just what she had thought of doing with me. After all, it's a big public event, relatively safe. She could even have her friends hidden around the grandstand to keep an eye on us, to make sure I didn't turn out to be a complete jerk.

But, all for naught. Dejected, I rode over to the base of the sledding hill, walked my bike up it, and sat in the grass where I could see over the fence as the races started. I had never seen the races before; I had only heard them from my house. To say they were loud from home took on new meaning as the first race commenced; the noise here was deafening. I got lost in the spectacle of the races until she emerged from the sea of parked cars at the bottom of the hill and headed toward me. Play it cool, man, play it cool. Wipe that massive smile off your face. Of course, I couldn't.

"I thought you didn't go to the races?" she said as she walked up and sat beside me on the grass.

"I don't."

"Oh, what are you doing here then?"

"Well, uh, just a coincidence."

"Not because I mentioned them?"

"That might have something to do with it. I, didn't catch on at the time."

"I'll say."

"Look, I'm not used to pretty girls talking to me."

"'Pretty girls'?" She emphasized the plural.

"Well, one pretty girl, at least." I looked at her and smiled a stupid, crooked grin. She smiled back.

"So, you think I'm pretty?"

"Well, obviously. "

"I'm not sure it's been that obvious."

"Oh, sorry. Well then, yeah, I think you're very pretty."

"Good. Because I still think you're cute." She slid over and closed the gap between us. I was nervous. I had never been in that much contact with a girl I fancied like this before. Well, not when we were alone, anyway. Sure, she had sat on my lap in class, and we had been in more or less this same position on a bus, but nothing could have happened then. Now...

"Uh, so, how'd you find me? I was looking for you earlier, hoping to spot you in the crowd, but I clearly didn't."

"I saw you riding around from up in the grandstand. My family is all up on the top row on the right."

"I know your sister. We've had classes together plenty of times."

"I figured you did."

"So, you didn't ask her about me too?"

"Are you kidding? And be exposed to the relentless taunting of my younger sister because I'm asking about some boy in her class."

"I guess not."

"Of course I asked her about you."

"And?"

"I'm not sure I should be sitting here with you."

"I'm that bad, hu?"

"Only your reputation. She thinks you're actually a decent sort of guy."

"Well, that's nice to hear. You come across fairly scandal fee, by the way."

"Do I?"

"Yeah. Asking about you mainly gets back, 'The read head? She's nice, I guess.' So apparently, you keep a low profile."

"Who were you asking?"

"Just people I know in your class. I don't know how well they know you, if at all."

"See, it's not so weird I was checking up on you."

"No, I guess not. Though, speaking of checking up on, shouldn't you get back to your family before they start wondering what happened to you? Not that I want you to go."

"No, I have a little more time. I usually wander off to find friends, so my being gone is nothing unusual."

"That's good."

"Why is that good?"

"Well, I like it when...," she leaned in and kissed me, "... you're around. Wow." She smiled sheepishly.

"Do you?" I leaned in and kissed her this time. She kissed back. The grass on the hill was long, and green, and soft. The leaves in the birch and maples were verdant and gently rustling. The dark green of the pines and their resinous scent are forever etched in my memory. All offset by the rusty red-orange of Ashleigh's hair at that moment. And then she stood up and started to walk down the hill.

"Hey! Where are you going?"

"Don't want my family wondering where I've gotten to."

"Well uh, hey, can we, I mean, you know, maybe sometime..."

"I'll see you in class tomorrow." And she was off and gone.

I hung around on the hill for as long as I could. I spotted her once she got back up to the top row of the grandstand, but eventually, it was getting dark, and I needed to go before I got into trouble for staying out too late. I might have been eighteen, but as I still lived at home, I wasn't yet free to set my own rules.

That Monday morning at school I was nervous. I had really, really liked kissing Ashleigh, and I fancied her like mad. But having had the entire weekend to overanalyze things, I figured whatever I was about to do was going to screw everything up. I entered the music room with some trepidation only to find I had beaten her there. I sat down in my usual place and anxiously watched the door. She came in, and our eyes met. I smiled. She smiled. Okay, so far so good. I hadn't messed up yet. She sat down in her usual place. Okay, what do I do now? There's nothing unusual about any of this, but we kissed two days ago. Do I go over and talk to her, or is that too forward? Maybe I should stay here, or is that ignoring her? Before my mind had finished tormenting itself, she stood up and walked over to me. She sat on my lap again; this time, her butt was right above my crotch. She turned slightly, and instead of putting her hand on the back of the chair like she previously had, she put her arm around my shoulders. She leaned in kind of close.

"Do you ride a bike a lot?"

"Yeah. I have a car but have to share it with my brother."

"Egh, I know what that's like. Well, it's supposed to be nice Wednesday evening. You might want to go for a ride."

"And, is there any particular place I should go on this ride?"

"They say the catholic church is fun around 6:30."

"Oh, well, nothing new then. I'm always cruising around the churches on Wednesday nights." She laughed and went back to her seat. The following 48 hours passed very, very slowly.

Wednesday was a wonderfully pleasant late May day; it was warm but not quite hot yet, with a bit of a breeze and scattered puffy clouds that didn't threaten rain. Almost an as perfect day as you could want. I was on my bike doing laps around the catholic church at quarter past six. There were a lot of people coming and going, same as at all the other churches in the area; I guess it's the night all christians indoctrinate their young regardless of dogmatic variation. Eventually, I saw her coming from a few blocks away and hoped the church was not our destination. It wasn't. She spotted me, and we took off together.

We chatted as we aimlessly rode around. We rode near her house so she could point it out to me, but not so close as we would be spotted by her family members. Then we did the same thing for my house. There were streets we couldn't go down because friends lived on them. Apparently, we didn't want to be seen together. I'm not sure why. Maybe her family had strict rules against her being with boys. Perhaps she didn't want to be the subject of gossip at school. That was probably a force of habit at this point; after all, she was graduating in two weeks, so what would it really matter to her? As for me, I didn't care if people saw me with her. I thought she was terrific.

Eventually, our route meandered into the fairgrounds. Much quieter on a Wednesday evening. We rode through its deserted grounds and out the back entrance, and instead of heading down the road back into town, we turned the other way, around the gate blocking the road, and up to the top of the hill where the water tower was located. The sun, though blocked by trees, was starting to get low in the sky, the clouds were beginning to take on the tint of sunset, and the water tower was starting to tinge yellow and orange.

"Have you ever walked any of the trails up here?" I asked Ashleigh.

"No. I didn't know there were any."

"Oh yeah, loads of them all over the hill. Bet we could get a good view of sunset if we headed off that way." I pointed in a particular direction where the grass was partially trampled down. She agreed that sounded like something good to do. We ditched our bikes under a tree and scampered through an old barbed wire fence that failed to keep anybody or anything away from the water tower. She took my hand as we walked along.

The top of the hill was tall green grass interspersed with small trees slowly encroaching from the forested hillside. The trails, undoubtedly made by generations of kids running around up here, crissed and crossed and weaved and dodged in and out of the trees, around steeper spots and over small mounds, were sometimes bare dirt kept clear by the repeated traverse of bicycle tires and were sometimes just grass trampled flat underfoot.

We reached the crest of the hill where the vista opened before us to the northwest. The hill was just a hill, not a mountain or some breathtaking topography worthy of recognition by the masses. It rose one hundred feet over the surrounding town and fields if that. But seeing the sunset on Ashleigh's ginger hair as she stood in the tall green grass was worth all the breathtaking views in all the national parks' to me. You can have them as long as I can have this.

We looked at each other and kissed again. Then we kissed some more. Then we stopped and looked around and listened. Hearing nothing but the breeze in the treetops and seeing nothing other than the swaying of the tall grass, we kept kissing. Eventually, ending up down in the tall grass. I was very content with what was happening. Ecstatic even. Oh, to be sure, my lust for this girl with the Irish last name was in overdrive, but I didn't expect anything beyond this. I hadn't even expected to make out with her like this. But Ashleigh, oh, Ashleigh, I had greatly underestimated her lust for me.

We rolled in the grass; our hesitant kissing had progressed to full-on making out, tongues flicking, probing, necks being kissed and playfully bitten, hands just starting to explore around the parts of the other's body where they weren't very likely to get slapped away, giggling the entire time. On one of these frequent rolls, she gained the upper position, and to my surprise and delight, instead of laying long in the grass next to me, she climbed atop me, straddling me, crotch to crotch. We were still fully dressed, but I was so aroused I figured she felt my erection even through two layers of denim. She slowly bent forward, rubbing her hands over my stomach, pushing up my shirt as her hands ran over my chest and then up my arms that were stretched out over my head. Her ginger hair cascaded down over my face, and she kissed me as our lips came into reach. She slowly sat back up, her hands making the reciprocal journey over me, leaving my shirt pushed up until she sat upright again. Her hands didn't stop. They went to the bottom of her shirt and then, quickly, flicked up over her head, shirt in tow.

My eyes must have been tremendous as they strove to take in every single photon that was bouncing off of her breasts, partially covered in a shockingly red bra. She spoke.

"I hope you don't mind."

"No. Uh, no. I don't, no, uh, mind at all. I like this. You. A lot. I like you a lot."

"Good," she said as she leaned back over and kissed me again. I felt the fabric of her bra on my chest and slowly put my hands on the bare skin of her sides. I wanted to touch her breast. Oh fuck, how I wanted to get my hands all over them, squeeze them, suck on them. But I didn't know if it would be going too far, so I didn't.

We kissed, and we moaned each other's names softly as we did; I didn't mind being called Marcus when it came from her lips. She started to grind her hips on me. It was so incredible. I knew she felt the massive erection in my pants. She sat back up and continued to rub on me. My hands went to her waist and spurred her on, but she didn't want this. Her hands came down, took mine, and placed them over her breasts. She humped, and I fondled. Her hands disappeared behind her back, and the red lace fell away into my hands. Her mounds of pale flesh were exposed. Her pink nipples and areolas were tight, aroused, and arousing. She smiled a wicked grin as she leaned forward again and kissed me, sucking on my tongue hard before sliding forward so her breasts were right in front of my face. I took it as an invitation and sucked one of her nipples into my mouth while my hand found the other. She gasped and then moaned as I sucked and kissed her breast. She presented the other to me, and I repeated the actions, all the while wondering if I was about to cum in my pants.

She sat up again, and my hands stayed firmly affixed to her breasts, interchangeably playing with her nipples and gently squeezing the soft mounds. She reached down and unbuttoned her jeans; I can still hear them unzip. I looked and saw the fly spread apart to reveal the top of a red pair of panties. She started to grind against me again as her right hand slipped beneath the red fabric. Oh god, she was masturbating on me. I wanted to unbutton my own jeans and pull my cock out and stroke myself off all over her. Better yet, I wanted her to do it. I watched as her hand reemerged and was joined by the other, pushing down the top of her underpants, revealing the same ginger hair as that which cascaded from her head. The curtains matched the drapes. She let go, and the elastic waistband flicked the panties back into place. My hands left her breasts and moved lower. Her hands left her crotch and found mine. She fumbled with the button on my jeans as my fingers found their way into her jeans. My zip unzipped, and I felt her hand slide along the bottom of my shaft, pushed upwards, straining in my boxers.