Prom Date Ch. 01

Authors note: Thanks to Chief Hal for the proof read.

No characters in this story involved in any sexual situation, encounter or act are under the age of 18.

This is a first time story. I hope you all enjoy this and the rest to come.

Chapter 1

I was headed across the parking lot, heading home for the day. I was glad high school was almost over. I'd only been at this school for a few months; but, it took a lot less than that for me to get a reputation, and not a particularly good one. I'm a math nerd, I love math! I can count on math to always be there, and always be truthful. I wasn't as lucky with girls at my last school, and I was glad to be moved to a new city and start over. Unfortunately, my first attempt with girls at this school, failed as miserably as they had at my last school.

I was almost at my car, an old, and I do mean old, 1969 Ford Thunderbird. That was the other thing I was really good at. I'd rebuilt the ancient two door sedan from the ground up, taking an old junker that had been sitting in a barn for decades, and stripping it down and rebuilding everything from the 429 cubic inch, 360 horsepower, gas guzzling monster of an engine; to the plush interior of the former luxury car. I loved the sound of the massive engine idling with a body thumping rumble. I would have thought it would attract girls, but for some unexplained reason, either it didn't, or they just didn't want to be seen with a math nerd.

"David!" I heard Lilly Crowell call across the parking lot. At first, I thought she was calling for someone else and ignored the first call, only turning on the second call. How did I know it was her? Hell, what guy wouldn't recognize the voice of the head cheerleader? I turned to see the blonde bombshell headed toward me at a fast walk. Each step made her grapefruit sized tits bounce in her powder blue V neck shirt and her long blonde ponytail swish, side to side like a metronome. I could tell she was slightly out of breath, as she headed toward me, her dark, red, lipstick covered, lips parted as she breathed heavily. I waited, taking in the look of the sexy cheerleader, her bare legs sticking from beneath the short powder blue skirt as she walked between the cars toward me. "Good, I caught you." She said cheerfully, as she walked closer.

"Yeah...you did." I agreed awkwardly. I honestly had no idea what she could possibly want from me. I wasn't part of any crowd, let along the IN crowd.

"I heard you had something you wanted to ask me."

"I did?"

"That's what I heard. David has a really important question to ask you. That's what Jenny said."

Jenny; one of the other cheerleaders. Tall, slender, toffee colored skin, shoulder length black hair, oh yeah, BIG tits for a slender girl. I had to admit that I loved to watch her tits bouncing in her cheerleader outfit, at the games. It was most fun at the football games, but now, volley ball was the only way to watch them. My mind snapped back to reality and off Jenny's tits, as Lilly reached out and touched my arm.

"You okay?" She asked, with a curious look on her face.

"Uh, yeah. I was just trying to think of what it was I needed to ask you. I must have forgotten." I lied. I knew damn well I didn't have anything to ask her, let alone tell Jenny that I had something to ask her. She was WAY out of my league and, while I didn't want to insult her, I had no idea what game was being played.

She gave me a frown and shook her head. "Typical boy, all talk and no do."

"All talk and no do?" I mumbled to myself. I looked at the sky and rolled my eyes. I took a deep breath and let it out. I had indeed made a comment in the hallway to one of the few friends I'd made since moving here, a comment never intended to be acted on. I looked back at her and shook my head slowly, hoping she had some other idea in mind, not that wild off the cuff statement.

"Weren't you talking to Greg and saying that if I didn't have a date to prom you'd ask me in a hot second?"

I had indeed said that, only three days ago. I shrugged and nodded. "Yeah, I did say that."

"Did you mean it?"

"Well, uh, not that you'd say yes or anything, but I suppose if you weren't going, I'd be tempted to ask."

She grinned a little. "Really? You think I'd go to prom with you if you asked?"

I shook my head wondering what game she was playing. "Actually, no, I don't think you would." I closed my eyes for a fraction of a second, as I let the thought ripple through my mind. Numbers flowed along with it, and in moments I was estimating the probability that she would say yes if I asked. The number was disturbingly low.

"You don't? Maybe you should ask and find out."

"First off, you're already dating Jason, everyone knows that. Second, Jason could break me in half without thinking twice. Third...well, Lilly, I'll be honest. I know what kind of a reputation I have. I'm great at math, not so great at personal relationships. And you have a much different reputation. You're a stuck up...well, I suppose I shouldn't say any more than that. It wouldn't be particularly nice."

"True, I do have a reputation. But maybe a reputation is just that. Not necessarily based on reality. And maybe, you have some hidden talent you don't even know about, that someone else would find attractive. Maybe you're more than a math dweeb. Maybe you're a kind, sweet, helpful, good-looking guy, that just happens to be good at math and is a bit shy. Maybe your reputation doesn't match how you really are? You're a new kid. It's hard to break into a new school, socially. I've seen you around. I watched what happened when you bumped into Tina that day. You stopped, and made sure she was okay and then helped her get her stuff back, picked up and to her class, even though you were late to yours. That's the kind of thing that makes a girl look twice."

"I don't know. I wasn't in the popular group at my last school either. After eighteen years, I think I've pretty much exhausted all the talent searches."

"Maybe you don't know all your own talents. According to Jenny, you have some assets that are worth taking a look at."

Now it was my turn to look at her curiously. "What assets?" I asked, in total confusion.

I saw her eyes dart down to my crotch and a little grin show on her lips before she said, "Let's not worry about those right now. Let's worry about that question you wanted to ask. Go ahead! Ask me, you might be surprised."

I frowned and shook my head. "Yeah, sure, why not. You wanna go to prom with me?"

"Yeah. I would." She said quickly.

"What?"

"I said yes," She said, standing there with a smile. "Give me your phone." I dug it out of my pocket and handed it to her. She rolled her eyes and turned it toward me so that it would see my face and unlock. She typed on it a few moments and then handed it back to me. "Call me later and you can take me out for a snack tonight. Wouldn't want to go to the prom having never gone on a date, would you?"

"I've been on dates."

"Not with me, you haven't," she called back, as she walked away, her pony tail swishing side to side.

Shit. Had I just asked one of the most popular girls in school out to the prom? I was pretty sure that's what I'd asked. The odds that she would say yes were down in the low single digits, and yet, she had. She had said yes! The only thing I could think of was that somehow, I didn't have all the pertinent data. Something in the equation had changed and I was missing crucial data. Jenny! That was the factor I needed. I needed to talk to Jenny and figure out what I was missing. This shouldn't have happened. There was no significant chance she would say yes if I asked; let alone come seek me out, to get me to ask. This defied my calculations, and since numbers never lie, I had to be missing numbers.

---o---

"This is really sweet!" Lilly said, as she sat next to me on the split-bench seat of my Thunderbird. "It looks almost new!"

"Thanks!" I said, with a huge smile. "Did it all myself."

"All of it?"

"Yep. Rebuilt the engine, trans, differential, brake system, the interior, even the upholstery."

"Wow. That takes some talent. Where did you learn to do all that?"

"Oh, I never did. I just sorta teach myself. Find a book or two to read."

"And you did all this...yourself...with no help? That's...well, amazing."

"Thanks." I said as I fired up the big 429 and gave the pedal a stab to make it growl the way only a big block can do. Not like those wimpy little four bangers so many guys drive around, sounding like a bunch of angry bumblebees. I dropped it into reverse and backed out of her driveway. I started us out toward McDonalds with a low rumble of exhaust. "So, you know I have to ask. Why me?"

"Why you what?"

"Lilly, I just want to be straight up here, I don't want to get killed by Jason."

"Oh, you don't have to worry about him. Jason and I broke up."

I looked at her curiously. "You two broke up? Why?"

She looked at me with a frown. "Do you want me to go on a date with you or not?"

"Well, what guy wouldn't. But you have to see it from my side. This is kinda out of the blue and, well, guys like me don't date the most popular girl in school."

"Well, maybe I want something different, for a change."

"Okay, so he dumped you for another girl."

"I didn't say that."

"You didn't have to. It adds up. Highest probability factor is you dumping him for another guy, or him dumping you. Given he was hanging all over Samantha Green today, well, it figures."

"That obvious?"

"Only if you're looking."

"And everyone is looking?"

"So, this is a spite date?" I asked quietly.

"If I said yes, would you be hurt?"

"No, I actually assumed it was something like that. As long as I'm not getting pounded by Jason, I'm fine with it."

She looked at me curiously. "That's an interesting attitude. It doesn't bother you that you're a spite date? That I'm just using you to send a message?"

"The way I see it; you're not actually going to stay dating me after prom. This is gonna be a whirlwind romance, so to speak, and after prom is over, I'm gone. You get your message sent and then either get back together with him, or go off and find someone else. The probability of you continuing to date me after prom, is over is extremely small."

"Do you think of everything as a math problem?"

"Not everything. Most things. It makes it easy for me. Numbers never lie."

"And your assessment of us, you and me, is not good? Why not? Maybe I'm into someone more like you."

"Probably not. The way I figure it, you already bought the dress, and you can't not go. Everyone expects you to be there. I'll be surprised if you're not voted in as prom queen. The odds are in your favor for that as well, especially if you bring someone like me as a date. You need to go with someone that won't upstage you or make you look bad. Dating someone in a lower caste makes sense, it makes you look like you're not lost without him. The only question that remains, is why me, in particular. Why not someone a little more cool or whatever we want to call it."

"You're pretty good at figuring things out, aren't you? You're right. I was planning on dumping you after prom. And it's you, because Jenny heard you telling someone you'd take me if I wasn't going with Jason. I didn't figure you'd say no."

"Good. I like knowing where I stand." I said, as I rolled into McDonald's parking lot. "Drive thru or in."

"Drive thru is fine. So, you're okay with us dating only 'til after prom?"

I nodded and we went through the drive thru, got some food and then headed down to the city park to talk and eat. We were about half done eating when she blurted out. "Have you ever kissed anyone?"

"Sure I have." I answered honestly. "Before I moved here, I had a few girlfriends."

"So, you can kiss. Show me."

"Huh?"

"Show me, you can kiss. I don't want to be stuck at prom with a guy that doesn't know how to kiss! Kiss me!"

I shrugged and set my sandwich on the dash and then leaned over toward her. I leaned my face to hers and gave her a soft kiss on the lips that lasted no more than two seconds, and pulled my face back.

"Wait, that's it? You didn't even give me a chance to kiss back."

"I...um...I was..."

"If we're going to do this, you better learn how to kiss. That'll be my payment to you, for taking me to prom. Teaching you how to be with a girl. Now do it again. Longer this time."

I leaned toward her again and pressed my lips to hers. Before I could pull back, she wrapped her arms around my neck and held me in place. I wasn't sure what to do exactly, but decided to follow what she was doing to me. She eased her grip around my neck enough, we could move our faces, but was still sure I wasn't going to pull away. She softly kissed my lips and then spread hers slightly. I felt her tongue press to my lips, flicking across them, coaxing me to open my mouth, which I did. Her tongue dipped into my mouth and teased the tip of my tongue. Several times she stuck her tongue into my mouth and then pulled it back. After the fourth time I realized she wanted me to do the same. I stuck my tongue into her mouth and she closed her lips on it and sucked it for a moment before letting me go. She stuck her tongue into my mouth again and I sucked it, like she had.

After several times swapping sucking, and teasing each other's tongues, she sucked my lower lip, pulling it and at the same time, pulling me toward her. She slowly leaned back, making me twist to stay with her, until she was leaning back at an angle, her head resting against the door. I was half laying on top of her, kissing her, for at least ten minutes before she let me go, both of us panting heavily.

"Okay, now that's a kiss!" She breathed, as I continued to lay half on her. "How about we move to the back seat and try it again? I'm sure it's more comfortable back there."

"Sure," I readily agreed. How much trouble could we get into kissing? I moved off of her to climb out of the car, but she just climbed over the seat and flopped onto the big back seat on her back and then looked at me expectantly. I looked at her lying on the back seat, her tits pushing two large mounds in the sweater and her legs slightly spread with one foot on the floor and other leg laying on the back seat, stretching the short skirt hem tight. I could feel my, already partly hard, dick grow even harder. I climbed over the seat, ending up laying on her, between her legs, with my hard dick pressing against her pelvis. I could feel my hard dick, bent uncomfortably in my pants, pressing against her, and knew she felt it as well, arching her back slightly to press her pussy against my bulge.

"Sorry," I whispered.

"For what? You think a girl doesn't expect a guy to get hard kissing like that? She'd be disappointed if he didn't."

"Oh."

"Would you like me to fix it?"

"Fix it?"

"Yeah silly. It can't be comfortable that way."

"It's...um, no, it's not."

She smiled and whispered. "Just relax. I can tell you're really nervous."

"It's kind of hard," I answered, as she reached between us, her fingers trying to worm to my pants front.

"Lift up a little so I can do this." I lifted myself onto my hands and knees over her, my arms shaking as her fingers found my belt and started to undo it. "Haven't you ever been with a girl before?" She whispered softly.

"Well, um, sorta." I answered.

"Have you ever been with a girl that touched you?" She asked curiously.

"Um, actually, um, no." I admitted, feeling my face warm, as I blushed in embarrassment.

Her fingers continued to fiddle with the front of my pants as I held myself over her, the zipper and snap of my jeans undone. She used her hands to push my pants part way down my hips, moving them down far enough to let the huge bulge in my briefs protrude in the vee of the front of my pants. She gently slipped her fingers into the elastic band of my briefs and gently tugged it outward, allowing her other hand to slip into them. I felt her straighten, then grasp my hard-on with her whole hand. "My, you are hard." She whispered. "Do you like this?" She started to gently stroke my cock with her finger tips, running them up and down the shaft and over my engorged mushroom head. To say I liked it would be a huge understatement. I'd never had a girl touch me in any way, let alone like this. Her finger tips stroked up and down my shaft, then circled and teased around my engorged, mushroom head. She let one fingertip stroke across the very tip of my dick, collecting the slick precum there and smearing it around my head and across that sensitive spot under my head.

"Oh damn," I groaned.

"I'll take that as a yes. Now, why don't you try that kiss again?"

I leaned my face down to hers and gently kissed her lips while she stroked my dick. I did my best to be as gentle and seductive with my kiss as she had been, in the front seat. I found it very hard to concentrate on kissing her while she teased my dick. I felt that urgency start to build and suddenly realized that she was about to make me come. "You have to stop." I grunted, as I pulled my face from hers.

"I do?" she asked, looking back at my face from only a few inches away. I could see a smile creep to her lips, as her fingers continued to stroke me. "Why would you want me to stop?"

"Cuz you're going to make me come." I panted, curling my toes to try and stop what started to feel inevitable.

"Really? It feels that good?"

I pushed myself up and reached between us, grasping her hand to stop me. "Please," I grunted, trying to stop her. Instead, she grasped my dick with her hand and held me, not letting me pull her hand away. She pushed my briefs down further with her other hand, forcing them and my jeans lower so that my entire butt and pelvis were exposed. She let go of my briefs with her other hand and reached for mine. She pulled on the hand I had gasped hers with, and pulled it down between her legs. She pressed my hand up under her skirt until my fingers were pressed against the crotch of her panties. The material was warm and damp, and as she pressed my fingers against her, she arched her back a little.

"Why don't you touch me back?" I held my fingers against her pussy, unsure what, exactly I should do. "Haven't you ever touched a girl down there?"

"Well, I put my hand down one of my girlfriend's pants. But we didn't do much."

"Well, pull my panties down a little so you can get your fingers under the crotch material, and then you can touch my pussy."

"Okay," I said nervously. She lifted her butt and I was able to pull the panties down a few inches, the crotch now easily pulled out of the way. I couldn't see under her skirt, but I could feel. Her pussy lips were very soft and warm, and surprisingly wet. I stroked a finger up and down the soft lips, letting the moisture spread all over her lips, while she shifted her grip on my dick again, releasing it so she could tease her fingers on it.

"Now, use the tip of your finger to push between my labia and stroke inside me. Be gentle. Girls don't like being roughed up."

I followed her direction, sticking my finger between her lips and moving it up and down. I worked my finger down lower, and felt the entrance to her vagina, and as I stroked back up, I felt the hard little bump that was her clit. Each time I stroked across it, her body pushed back at me, her back arching, pushing her pussy toward me.

"Pull my skirt up," She whispered, arching her back and lifting her butt off the seat. I shifted position and pulled the short black skirt up her body, until it was bunched up, around her waist. She set her now bare butt back on the seat and started teasing my dick again. I went back to stroking her pussy with my finger, teasing from the entrance to her vagina to her clit. "Push your finger in when you stroke down there." She whispered breathlessly. "That's it, just like that!" She said, as I pushed my finger slowly into her depths, pushing it in a little more than two knuckles deep. I pulled it out and stroked up to her clit, then let the tip of my finger circle her hard nub.