My Best Girl

[ mf, cons, tv, slow, rom, teen, oral ]

mandysdad@rocketmail.com

Published: 22-Apr-2013

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This work is Copyrighted to the author. All people and events in this story are entirely fictitious.

Winnie Cooper was my best girl. We'd known each other practically our whole lives, growing up on the same street in the same middle class American neighborhood. I'd taught her how to play stick ball and she'd taught me how to play hopscotch. We'd played doctor when we were seven years old; I showed her mine and she showed me hers, and she even let me touch it with my finger. When we were twelve we shared our first kiss, and it had been just as magical as I'd always thought it would be. In fact, it had even been more magical than I'd expected.

It was near the end of the summer of 1968, and Winnie had just found out that her brother Brian had been killed in Vietnam. Naturally, she was filled with grief, and she'd gone off to be by herself, but I knew somehow that she didn't really want to be alone. I found her at the park, sitting on the oddly low branch of a tree, and without any words we began to kiss and make out. Tentatively, I'd touched her breast (the first breast I'd ever touched in my life), and she'd let me. Then she let me put my hand inside of her blouse and touch her, skin to skin, while we kissed. Then Winnie, still wordless, had unsnapped the fly of her jeans and guided my hand down into her pants. I slipped my hand into her underwear and touched her pussy (the first pussy I'd ever touched too). She was mostly smooth down there, though I could feel a little bit of pubic hair. While I rubbed Winnie between her legs, amazed at how soft and warm her lips were, she rubbed me too, fondling my sudden erection through my jeans. In an amount of time that had seemed like hours and yet only seconds, Winnie had come, holding me tight as she shuddered and trembled. Then, still with no words passing between us, Winnie unfastened my fly, took out my cock, and stroked it a total of eight times before I experienced my own orgasm. My come squirted out of my cock and spilled all over her hand, but she didn't seem to mind, or even be surprised.

That had been our first sexual encounter, and the whole time we hadn't spoken to each other at all.

It wasn't our last sexual encounter, though. Winnie and I were a couple on and off ever since then, and though we never progressed as far as oral sex or intercourse, we did some other things that served to keep the demons of our erotic passions at least somewhat mollified, if not entirely at bay. We masturbated each other a lot, both of us growing very accomplished at giving handjobs, and a few times Winnie had even stripped down to just her underwear and let me dry hump her.

It wasn't usually the sexual tension between us that caused the frequent break ups we had; mostly it was other stuff, misunderstandings, confusions, dumb mistakes, mostly on my part. But the break up we had in the early spring of 1972, one of our more serious breaks, had everything to do with sex. Or the lack of it.

I hate to admit it now, but I was getting pretty frustrated with not being able to go all the way with Winnie, or even get any oral sex. I felt like we were old enough and mature enough to move on to that stage, but all along Winnie had steadfastly resisted. Then one night when I was over at her house, after yet another round of jerking each other off while we watched an old movie on TV, we'd fallen asleep and stayed the whole night together on her sofa. The next day the news of what happened got around, and when a few of the guys asked me if I'd gotten lucky, I, who had never so much as uttered a word to anyone about the sexual aspect of our relationship, just shrugged and said, "Use your imagination." That was all it took to ruin Winnie's reputation, and with it, I believed, went my chances of ever getting back with Winnie Cooper again.

*****

Two weeks after that disaster I was sitting in the school cafeteria with my best friend Paul, finishing up a fairly decent lunch and talking about the upcoming spring dance. It was only a week away and neither of us had dates yet. I wasn't too worried about it because I was still holding out a feeble and unrealistic hope that Winnie and I would work things out, but Paul looked like he was ready to jump out a window.

It was his own fault as far as I was concerned; he'd had a great thing going with Sherry Butler but, for reasons he never really shared with me, he'd blown it (maybe the same way I'd blown it with Winnie?) and they weren't a couple anymore, and now he didn't have a date. And because I was his best friend he was making me pay for it.

"I'm gonna die alone," he announced with the gravity of a judge sentencing someone to life in prison.

"Come on, Paul," I said. "You still have a whole week to find somebody to go with. How about Beverly Bosley? She's cute, and I don't think anyone's asked her yet."

"How would you know?" Paul asked, resorting, as usual, to logic. The truth was I had no idea, but that wasn't really the point; Paul had to stop feeling sorry for himself, otherwise he really was going to die alone. Or at least miss the spring dance.

"I'm just trying to help," I said. "And just so you know, you're not the only one who doesn't have a date."

Paul gave me a wry look, but didn't say anything; he'd heard the rumors too, and he'd known right from the start that they were a lie. He also knew that my chances of making up with Winnie were about the same as the chances of the Flying Nun appearing in the next issue of Playboy. I gave him my own wry look, then turned and checked out the rest of the cafeteria, not so much because I was interested in who was around as to simply not have to look at Paul anymore.

And that was when I saw her: one of the most amazing visions of loveliness ever to grace the face of the Earth. Her name was Jessica Thomas. Tall, blonde, gorgeous. Shaped like every guy's fondest dream. She was so beautiful it was hard to believe she actually existed, let alone went to my high school. But there she was in all of her pulchritudinous glory, standing almost shyly near the cafeteria door, her hands clasped together in front of her, apparently looking around for someone she knew that she could sit with. It suddenly seemed like a good thing that Winnie and I were on the outs.

"Only in your dreams," Paul said.

I looked at him. "What are you talking about? You think I can't get Jessica Thomas to go to the dance with me?"

"She's probably already got a date," Paul replied, which made way too much sense for me. "And even if she doesn't, she wouldn't go with you."

"Why? What's so wrong with me all of a sudden?"

"Come on, Kev. You know she only dates jocks."

I could always count on my best friend to destroy my dreams and tear my self-esteem to shreds. Fortunately, I wasn't the kind of guy to let logic or a sudden sense of inferiority stand in my way. I was going to ask Jessica Thomas to go to the spring dance with me, and that was that. If she turned me down, or worse, laughed in my face, then so be it. The way I saw it, the potential prize was worth the risk.

I took a moment to steel myself, ignoring Paul's "Don't do this, Kev, I'm telling you," then got up from the table and walked on legs I couldn't feel over to where Jessica Thomas stood. She was still looking around, now seeming more like she was lost than searching for anybody, and when her beautiful green eyes lighted on me I froze in my tracks like a deer caught in headlights. I willed myself to say something, but all that came out of my mouth was, "Uh."

Jessica smiled at me and I could feel all the blood leave my head.

"Hi," she said.

"Uh," I replied.

I couldn't look her in the eyes anymore so I looked down, resting my gaze on her magnificent chest (it was rumored that her bra size was 36C), and now all the blood that had left my head suddenly took up alarming residence in my crotch. I wanted to put a hand in front of it so she wouldn't notice, but that just would have called attention to it.

"Uh," I said for the third time, then literally forced myself to speak, "They're serving macaroni and cheese for lunch today." Actually, I couldn't remember what they were serving for lunch. "It's, um, it's pretty good."

Jessica, whose smile was already bright enough that it could be seen by the Apollo spacecraft, suddenly got even brighter.

"Okay," she said. "Thanks."

"You're welcome. Um. Enjoy your meal."

Jessica might have heard that last part, though if she did she heard it while she was waving and saying hello to her friends ten feet away.

I hated like hell to make that long walk back to the table where Paul was sitting.

"I told you," he said, shaking his head.

"You didn't tell me anything," I replied, not worrying that I wasn't making any sense. "I just choked, that's all. I'll get her to go out with me. You just wait."

"And how, exactly, are you going to do that?"

"Easy. I've got a plan."

*****

I didn't have a plan. At least, not right at the moment. But I eventually came up with one, and it wasn't really that long in development. I only had to wait until that afternoon, after my last class, when I was on my way from my locker to the exit and freedom, when I saw Winnie, and the solution to my problem suddenly appeared in my head.

Because Winnie wasn't alone; she was with Jessica Thomas. They were standing by Winnie's locker, books held up in front of their delectable chests (my best girl's chest wasn't nearly as well-developed as Jessica's but still, she had nothing to be ashamed of), and they were talking and laughing like old buddies. And that was when it hit me: if I couldn't get Winnie back, I could at least ask her to ask Jessica to go to the dance with me. It was a conniving, cowardly plan, showing a remarkable lack of sensitivity for Winnie's feelings, but still, it was brilliant, and I knew it would work. All I had to do was wait until the two were done talking and Jessica had gone on her unbelievably beautiful way, then Winnie would be alone.

I waited there in the hallway for twenty minutes, standing by some unknown person's locker, my school books getting as heavy as gold bricks, silently willing the two girls to shut up and go home already. But they just continued to talk and talk and talk. I was getting really annoyed, and was no longer relishing the opportunity to stare at the two prettiest (and sexiest) girls in school. I was just about to give up when I heard Jessica say, "Okay, I'll see you later." Then she pecked Winnie on the cheek and walked away and Winnie, either sensing my presence or having noticed some time ago how I'd been loitering near her like a pervert waiting to pounce, smiled at me and said, "Hi, Kevin." She was still holding her books, but now she lowered them until they were in front of her bellybutton, giving me a great view of the two tiny tents sticking up on her chest. It was probably a completely innocent gesture (Winnie, though she knew she was attractive, was still unaware of how gorgeous she was), but as always it got my dick standing at attention in a hurry. And for a moment knocked my brilliant idea right out of my head.

"Hey, Winnie," I said. Then I just stood there like a dope, grinning at her and staring at her tits.

"I'm up here, Kevin," Winnie said, waving to get my eyes to move up to her face. She was still smiling, though, so she obviously wasn't upset with me.

"Right," I said. I took a few steps closer to her. "Um, I have something I want to ask you, Winnie. A favor. But it's kind of a big favor, and I'd understand if you said no."

"Well, sure, Kevin. What is it?"

"Well, um, I was wondering if you could maybe ask Jessica Thomas if she'd go to the, um, spring dance with me."

I was fully prepared for Winnie's hurt and betrayed look; God knows I'd seen it enough times before, especially lately. But, as always, my best girl surprised me; instead of getting all teary-eyed and devastated (and throwing her school books at me, something that had happened before too), she gave me a remarkably patient and indulgent smile and said, "Okay, I'll ask her for you."

"Really?" I said, helplessly showing my surprise. "You mean it?"

"Of course, Kevin," Winnie said, reaching out and touching my arm. "Just because you and I didn't work out, doesn't mean we don't deserve to be happy. Right?"

"Uh..sure."

"I do have one condition, though."

"Condition?" I suddenly knew what that condition would be, I could see it in my mind's eye: in the next instant Winnie's beautiful angelic face was going to twist up into a grimace of hatred and she'd say, "Go fuck yourself first!" And then she would probably hit me and kick me before turning on her lovely heels and storming out of my life forever.

"Kevin? Did you hear what I said?"

"Huh?" I blinked. "You, uh, said there was one condition."

Winnie sighed and rolled her large dark eyes and said, "I said, I'll ask Jessica to go out with you if you ask Steve Bigcock to go out with me."

"Steve who?"

"Steve Biggs," Winnie said. She sighed again. "Honestly, Kevin, you're not a really great listener."

"Steve Biggs? You mean Steve Biggs the senior? Captain of the football team?"

Deflowerer of teenage girls everywhere?

Winnie brought her books back up in front of her chest and hugged them.

"Yeah," she said, "isn't he dreamy?"

"No," I said. I would have said so even if the question hadn't been posed by my former best girl, but because it was, I just meant it more.

"Well of course you don't think so," Winnie said, "you're a boy. Just like I don't think Jessica Thomas is sexy. Well, not that sexy, anyway. But whatever. If you promise to ask Steve, I promise to ask Jessica. Okay?"

"Uh, sure. That sounds great."

And it did, sort of.

Winnie blessed me with yet another of her amazing smiles and said, "Okay, see ya."

Then she turned and was gone, and I was left standing there in the school hallway, wondering if what I'd just done was the smartest thing in the world or the dumbest.

*****

I didn't have a problem finding Steve Biggs; I just followed the cheerleaders until I found the front of the line. He was tall, of course, and impossibly good-looking, well-dressed, muscular, and deservedly stuck up. Completely the wrong kind of guy for Winnie Cooper. Still, I'd made a deal with her, and I managed to disguise my contempt for this brainless Adonis just long enough to tell him that Winnie had told me that she liked him and wanted him to ask her to the spring dance. I'll give the guy credit: he actually knew who Winnie was, and even more, he seemed flattered that she would want to go out with him. I gave him her phone number, wished him good luck (at the same time silently wishing that he'd accidentally walk in front of a speeding bus before he got to a phone), then left as quickly as I could.

I rode my bike home at breakneck speed, thinking to call Winnie as soon as I got there. But just as I came in Mom, who was, as always, happily wasting her life in front of the stove, told me, "Kevin, Winnie just called. She wants you to call her back."

Now, I'd gotten home pretty fast, and unless Steve Biggs had run to the nearest phone to call her and ask her out, then Winnie would have to have some other reason for calling me. Namely, I thought, to tell me that she'd changed her mind and that she wanted me to take her to the dance.

I got to the phone in an instant, and dialed Winnie's number so fast that I don't now remember even doing it. The stupid thing rang three times before it was finally picked up.

"Hello?"

"Hey, Winnie, it's me."

"Hi, Kevin. I just got off the phone with Jessica. She said she'd love to go with you to the dance."

"Really? Great!" I said, though in all honesty I was feeling as much disappointment as elation.

"Did you ask Steve Bigcock about me?"

"His name is Steve Biggs," I said.

"That's what I said," Winnie replied. "What did you think I said?"

"Never mind. I asked him and he said he'd like to go with you. I gave him your phone number."

"Are you mad about something? Cause you sound kind of mad."

"I'm not mad," I snapped. "Did Jessica say I should call her or what?"

"Yeah." Winnie gave me her phone number, then said she should probably get off the line in case Steve might be trying to call.

"Fine," I said, and hung up on her.

I called Jessica right after that and, just as Winnie had told me, she said she'd love to go to the dance. She even giggled coquettishly.

When I got off the phone I'd forgotten all about my ill feelings toward my former best girl; now all my thoughts were about Jessica Thomas and what might possibly happen with her on our date. I went to my room and locked the door (my brother Wayne had a habit of just coming in without knocking whenever he wanted to) (so did my mom) and went straight over to my dresser. In the bottom drawer, underneath my socks, I had a couple of cleaning rags that I kept for purposes other than cleaning. I took one out and kept it in one hand while I used my other hand to masturbate, my mind conjuring up a multitude of ideas concerning what I'd like to do with Jessica Thomas.

When I was done I put the cleaning rag in my hamper, then went to my desk and took out my secret notebook. It was in this notebook that I kept a record of every girl I'd ever had a sex fantasy about and the number of times I'd fantasized about her. I'd been keeping the list faithfully since I was thirteen, and there were almost fifty girls on the list. Most of them were girls I knew (Winnie of, course, who had more points next to her name than any other girl on the list, and, though I felt embarrassed about it, my sister Karen, who was number two), but there were also the names of certain female teachers I had adored, or models, or singers or actresses (my favorites were Maureen McCormick from The Brady Bunch, Karen Valentine and Judy Strangis from Room 222, and Marie Osmond). Even Wonder Girl from the Teen Titans. I turned to the last page and carefully wrote in Jessica's name, and across from it, behind the right hand margin, I wrote the number 1. In pencil, of course.

*****

Everything seemed fine after that. At least until the next day when the four of us got together at lunch time. We sat at the same table in the cafeteria, me and Winnie on one side and Jessica and Steve on the other, situated so that we were all facing our prospective dates. The conversation was going great and everyone seemed happy, despite the fact that neither Jessica or Steve appeared to have more than two digits in their IQs, or that Steve and I, try as we might, couldn't keep our eyes from zeroing in on our dates' chests. Jessica was wearing a white blouse that was so thin I could see her bra underneath it. That, along with her remarkable flirtatious smile, was enough to make me glad I was sitting down, with my crotch hidden under the table.

I was managing to carry on a completely ordinary and forgettable conversation with her while envisioning in my head what I could possibly end up doing with those two magnificent breasts hanging so firmly, so beautifully above the lunch table, when Winnie's voice suddenly tore its way into my brain.

"What do you think, Kevin?"

"Huh? About what?"

"A double date."

"A what?"

Winnie gave me that long-suffering look of hers and said, "Steve's car isn't running, which means that you're the only one with a car, so we thought you could pick me and Steve up after you pick up Jessica. And since we're all going in the same car, we just figured we should double. What do you think?"

Was she out of her mind? What made her think I wanted to go on a double date at all, let alone with her and Steve? I wanted to be alone with Jessica, to be in a position where I could take as much advantage of her as she might let me. Having Winnie and her date along would completely ruin that. I could see it now: me and Jessica sitting in the front seat at Lookout Point, two feet of space between us, both of us uncomfortable to the point of misery, while Steve Bigcock introduced Winnie to the joys of womanhood in the back seat. It wasn't going to happen.

"Oh, sure," I said. "That sounds like a great idea."

And so it was decided. We would all spend the entire evening together, a couple of couples, and Winnie would have the time of her life while my balls turned blue.

*****

Still, I held out hope; there would have to be at least a few minutes in the evening in which I'd have Jessica all to myself, not counting the time between when I picked her up and when I picked up the interlopers. Hell, I'd make the time. After all, I was going on a date with Jessica Thomas, a girl known to do more than just shake a guy's dick until he made a mess all over himself. Not like some prissy girlfriends I could name.

I pulled up in front of Jessica's house right at seven o'clock, and before I could even get the car in park Jessica was already coming out her front door. She was wearing a white dress dotted with tiny pink flowers, a low neck line, and a hemline that showed off her beautiful legs all the way up past her knees. Jessica hurried down the front steps and across the lawn and I barely had time to get out and open the passenger door for her. She smiled at me, a completely amazing smile that made my knees weak. She thanked me, then got in the car. I shut the door, hurried around to the driver's side, and we were off.

It wasn't a long trip to Winnie's house, only about five minutes, but I figured it was long enough that Jessica and I could at least get to know each other a little bit. I tried to make conversation, asked her a few questions about her school classes and her family, but the only responses I got were half-hearted, almost disinterested. I even tried to talk about the weather, making some inane comment about how it might rain the next day, but all Jessica said was, "I don't like the rain," while she kept her hands planted in her lap and her eyes on the passing scenery.

Like I said, it wasn't a long trip to Winnie's house, but it was long enough for me to figure out that my unbelievably gorgeous date was boring. And I was going to have to spend the entire evening with this dunce. The good news, though, was that her conversational powers weren't what made her one of the most popular girls in school.

When I got to Winnie's house I went up to the door and knocked, and after a few moments the door opened and Winnie came out. She was wearing a bright pink dress with matching pink socks and black shoes. She looked nice but not too dressed up, nothing fancy, and yet she still looked just as stunning as ever. For a second I wondered about that, how this small, almost spindly dark-haired girl, who looked so much different than my tall, blonde and well-built date, could be just as beautiful and sexy. Apparently, beautiful and sexy came in many shapes and sizes. Of course, our history together might have had something to do with it too. Or it could have been nothing more simple than the fact that Winnie was a girl and I was a boy. A boy with a dick that got hard at the slightest provocation.

Not that there was anything about Winnie that could be considered even remotely slight.

"Kevin?" Winnie said. "Are you okay?" I blinked and looked at her. "You went off into your own little world again. And you were staring at my boobs too."

"Sorry," I said, not feeling sorry at all.

"I'm ready to go if you are."

"Sure," I said, forcing myself to smile, though inside I was feeling just a little bit resentful; why did we always have to wait until she was ready? And why was it that, whenever she said she was ready, she was never talking about screwing? This was the Super Seventies, after all, the Age of Aquarius, the Era of Free Love. Everybody else in the world over the age of eleven was doing it, but not Winnie Cooper. Handjobs, however well done, were apparently all she could muster.

I supposed I should have felt good about that, though; because if I wasn't getting anything from her, then the odds were good that Steve The Big Dick wasn't going to get anything, either.

I walked her out to the car, held the door for her while she got in back, then drove her and Jessica over to pick up Steve. He was waiting at the curb when we got there, climbed in back with a "Hey, guys," then immediately put his arm around Winnie's shoulders and pecked her on the cheek. I tried to see in my rear view mirror if he was keeping his hands to himself (and if Winnie was keeping her to herself) but I couldn't tell.

"Did you know," Jessica said as I put the car in drive, "that Mark Rawley picks his nose and then eats it?" She looked around the interior of the car, apparently expecting some kind of response, then said, "It's disgusting. That's why I won't french kiss him anymore."

Judging from the continued silence from the rest of us Jessica must have assumed that none of us knew exactly what to say to that.

I drove us all to the school, trying to listen to Jessica's occasional bleats of ridiculous conversation with one ear and trying to pick up any noise (like the sound of a popping cherry) from the back seat with the other. At the same time I tried to concentrate on driving safely, while in my mind I could see Steve Tinydick's hand sneaking between Winnie's knees, sliding up between her smooth pale thighs, and up under her bright pink dress.

Screw it, I thought. Let the guy find out for himself that a wet finger and a jerk job were the most he was going to get from Winnie Cooper. If he even got that much.

When we cruised into the school parking lot I could feel the relief pouring over all of us like a wave. I parked as quickly as I could and we all threw our doors open and nearly leaped out onto the blacktop. Everyone was talking again, each of us saying something that no one else was listening to as we made our way across the campus to the gym. I was holding Jessica's hand and trying not to stare at her chest while Steve had his arm around Winnie's waist, his hip bumping against hers, his eyes roving around, looking at all the other kids heading for the dance, smiling like an idiot. He reminded me of a guy I'd seen once at Silver Lake, posing for a picture next to a gigantic fish on a hook. Proud of his trophy and wanting everyone in the world to see it.

Winnie was the catch of the day.

But if that was true, then Jessica Thomas was the first runner up, and I didn't really have anything to complain about. Or at least I didn't have enough to complain about, especially if things worked out the way I was hoping they would.

As soon as we got inside Winnie asked Steve if he wanted to dance. He said yes, so I took that as my cue to ask Jessica if she wanted to get something to drink. Divide and conquer.

Still holding her hand, I led her through the crowd of dancing kids to the punch bowl. I managed to avoid being disastrously clumsy as I poured us both a glass of punch, although I did accidentally bump her boob with my knuckles when I handed Jessica her glass. She gave me a look that said she knew I'd done it on purpose and she wasn't entirely happy about it. Then we just stood there, silent and awkward as we watched everyone dance. I racked my brain for some kind of conversational topic but all I could think of was the song that was currently playing: Satisfaction by the Rolling Stones.

I turned to Jessica and said, "Cool song," but the music was so loud she didn't hear me. I shouted, "Cool song!"

Jessica looked at me and smiled and said, "Yeah."

More awkwardness, then I said, "An oldie but a goodie."

Fortunately, she didn't hear that.

The awkwardness went on until we finished our punch, then I asked Jessica if she wanted to dance. She said, "Sure," with that winning smile of hers, and immediately the Rolling Stones song ended and Mr. Peterson, my history teacher and one of the chaperones, announced that there would be a ten minute intermission between dances. I looked sheepish while Jessica rolled her eyes, then I rolled my own eyes when Winnie and Steve came over to join us.

"Hi, Kevin," Winnie said, blissful. "Cool dance, huh?"

"Yeah, just great," I said, sounding every bit annoyed as I really was.

Winnie noticed and scrunched up her nose like she smelled something bad. She clicked her tongue and said, "You don't have to be such a grouch. Dances are supposed to be fun." She glanced at Jessica, then looked back at me. "Maybe if you'd brought somebody with a brain you'd be having more fun."

Yeah, I know, it sounds gutsy and rude, but she said it in such a low voice that I almost didn't hear it myself.

"You've got room to talk," I said in an equally low voice. We were standing real close to each other now, close enough that we could lower our voices even more. "Your boyfriend's IQ is almost equal to his shoe size."

"He's not my boyfriend," Winnie countered. "And he's smart, Kevin. Just because he's a football player doesn't mean he's stupid. And I seriously doubt that your slut girlfriend's IQ is any higher than her bra size."

"Jessica's not my girlfriend," I said.

"No, but she is a slut," Winnie replied, a surprising amount of venom in her voice.

"She's not a slut."

"She's two sluts and a tramp."

"She's not a slut."

"They why did you ask her to the dance? Because of her scintillating conversation?"

"It's none of your business why I asked her to the dance," I said, despite the fact that Winnie had just hit the nail square on the head.

"Actually, you're right," Winnie said, crossing her arms over her small breasts. "It is none of my business. Just like you're none of my business, from now on." She turned around as if she meant to storm off, but then she just stood there, scowling prettily.

"What do you mean, I'm none of your business?" I asked. "What the heck does that even mean?"

"It means what it means, Kevin Arnold."

I glanced around then, sensing a strange shift in the atmosphere, and realized that our dates were no longer standing there listening to us fight about them. I looked around the dance floor and finally saw them; they were over near the door, not leaving, but apparently getting ready to dance. Then suddenly a slow romantic song began playing and they put their arms around each other and started to move to the music.

Winnie and I looked at each other, she rolled her eyes and I shrugged, then we went out to the dance floor and began to dance. We started out stiff and awkward at first, which wasn't surprising since we were so mad at each other, but then something unexpected happened: as the slow romantic song went on and our bodies swayed with each other we started to relax, to soften and meld together into the old sweet pattern of just being together. I pulled Winnie a little closer, tightened my embrace, and I could feel her small breasts against me, her warm breath on my neck. I could smell the familiar perfume in her lovely hair. I heard her sigh once, just a short sigh, and it brought back all those old feelings and memories, the things about her that I'd never really let go of. It surprised me to realize that I'd never given them up. I'd never given her up. I'd never even wanted to.

The song eventually ended and Winnie and I stood in the middle of the dance floor, looking at each other. I'd been a little afraid that maybe she wasn't feeling the same thing I was feeling, but now that I gazed into her dark beautiful eyes I could see the same deep yearning that I felt. The same longing, the same incomprehensible love. She had missed me too.

I didn't say anything. I just took her hand and led her away from the dance floor, over to a doorway at the back of the gym. We went outside and found ourselves in a dimly lit parking lot. There were about four doorways running along the back of the building, all of them in shadows, and I led Winnie over to the closest one. Unfortunately, it was already occupied by a couple, a tall good-looking jock type and a blonde girl who was on her knees in front of him. It took me a moment to realize that the girl was giving the guy a blowjob, and in the next moment I realized that the couple was Steve and Jessica. I heard Winnie gasp in surprise beside me and felt her squeeze my hand.

I should take a moment here to point out a few things: for one, Steve's last name isn't Bigcock, but it might as well be; and two, Jessica's breasts, which were hanging out of her dress and shining in the dark like two firm pale lamps, were even more magnificent than I'd imagined they would be; and three, Jessica could suck cock like a porno star. Part of me wanted to just stand there and watch, especially since neither Steve or Jessica seemed to be aware of our presence, but Winnie squeezed my hand again, then whispered in my ear, "We should get out of here."

I whispered back, "Okay," but I wasn't sure if Winnie heard me, since at the same moment Steve suddenly groaned and grabbed two handfuls of Jessica's gorgeous blonde hair. And in the next instant Jessica pulled her mouth off of his cock and come started to squirt all over her face. Just like in my fondest fantasies.

"Kevin," Winnie said, a little urgently, and tugged on my arm.

"Okay, okay."

We went back inside the gym, weaved our way through the crowd of dancing maniacs to the front door, then out. As we headed for my car Winnie asked, "Where are we going?"

"I don't know," I said. "Just some place we can talk." Which was not really the truth; sure, wherever we went, we would probably be able to talk, but that wasn't my goal. I had every intention of trying to get Winnie to do what we'd just seen Jessica Thomas do to Steve Biggs. Maybe even more.

Because it was time. Winnie and I had known each other all our lives, we'd been in love since we were twelve, we'd already done all those things with each other that we'd never done with anyone else. Besides, I was sixteen now and Winnie would be sixteen in just another few months; we weren't kids anymore. We were practically adults, and it was time we started acting like it.

I thought about all of this as I drove around town, Winnie silent in the passenger seat, her hands clasped together in her sweet warm lap. I wanted to tell her everything I was thinking, to let her know that I wasn't going to back off this time. I was going to insist. Heck, I might even make her do it. If it came to that, anyway.

I drove without really knowing where I was going, but when I found myself turning onto Blackbird Drive, the road that led up to Lookout Point, I wasn't surprised, and I didn't think Winnie was either; we'd spent a lot of time up there, challenging the boundaries of our relationship. We went up the hill in a nervous silence, though, and we continued to not say anything when we turned onto Lookout Point and drove past a few cars that were already parked, their windows fogged up. I stopped under a tree and shut off the engine and the lights, and for about a minute Winnie and I just sat there looking at the town far below us. Finally, she scooted over next to me and I put my arm around her shoulders and we looked at each other.

"So," Winnie said.

"So," I replied. We continued to look into each other's eyes for several seconds, then I said, "I'm sorry, Winnie. For all that stuff that happened before. I was wrong."

"It's okay, Kevin," Winnie said. "I forgive you. And I know you didn't mean to hurt me. You never mean to hurt me. I know you've made some mistakes but I have too." She paused for a moment. "You've always been so good to me, Kevin. And you're so cute. You've always been so cute. Sometimes I forget how lucky I am."

I'd never been under the impression that Winnie was a particularly lucky girl, but at that moment I wasn't going to disagree with her. If she felt lucky, that was fine with me. The question was, how lucky was I? And how lucky was I going to get?

I leaned closer to her, closed my eyes, and I could sense Winnie doing the same. After what seemed like an overly long moment our lips touched, and there was that old familiar excitement suddenly pouring through me. Not just a sexual excitement (though there was that) but the excitement I'd always felt when I was with Winnie, holding her and kissing her and touching her. That same excitement that had blossomed the first time we'd ever kissed, the first time I'd held her breasts in my hands. Being with Winnie had always felt like a brand new thing.

How could I have ever even tried to pick Jessica Thomas over her?

Winnie murmured against my mouth as we kissed, and murmured again when she felt my hand touching her breast. As always, she seemed a little reluctant to let me do that, but in just a few moments she relaxed, and even started to like it. I fondled her small firm tit through her dress for a while as I french kissed her, then slowly but surely, I slipped my hand down the top of her dress, wormed my fingers under her bra, and began to caress her bare breasts. Winnie's little nipples were already hard and as I fondled her they seemed to get even harder.

She was breathing through her nose now, getting more excited, and her hands too were moving around. I could feel her fingers caressing my back, my shoulders, sliding up through my hair. Winnie liked to go exploring in all the safer places before getting to the heart of the matter. That was okay with me; it gave me more time to play with her boobs.

My hardon was getting impatient, though, and finally, finally, I felt one of Winnie's hands slide down over my leg, and then over my ridiculously hard cock. She rubbed me through my jeans and I took that as my cue. I broke our kiss, took my hand out of her bra, and leaned back against the car seat. At the same time I pulled Winnie closer to me, letting her rest her head on my shoulder as she used her other hand to get my fly open. She did it with amazing, practiced ease.

My cock literally popped out at her, and Winnie wrapped her fingers around it, then began to slide them lovingly up and down the shaft. I thought about the very first time Winnie had touched me like that and I'd gone off after only ten seconds, and I was afraid the same thing might happen again, it felt so good.

I kissed the top of her head, buried my nose in her dark sweet-smelling hair, and closed my eyes. I luxuriated in the sensation of getting a fantastic handjob from my best girl, feeling like the world was once again, at least for a short while, making sense. But then it all changed again.

Winnie's fingers danced along my cock for only about a minute before she slid them down to the base, right above my balls, and then she lowered her head until her soft cheek was resting against my stomach. Then, in the next instant, I felt something I'd never felt before in my life: a warm wet mouth sliding down over the end of my cock. Winnie was actually putting my cock in her mouth.

At first I wasn't really sure it was even happening, but the sensations that were coursing like fire though my groin couldn't be denied; Winnie Cooper really was giving me head. And she was, as far as I could tell, very good at it. Granted, I didn't have any experience from which to draw a sound conclusion, but it didn't take a Casanova to notice the skill and confidence with which Winnie performed.

She bobbed her head rhythmically on the end of my cock, using her tongue and her lips to induce the most incredible pleasure I'd yet felt in my young life. At the same time she moved her hand up and down the shaft in tandem with the movements of her mouth. She was breathing calmly and evenly through her tiny nose, her eyes lightly shut, her whole body seemingly relaxed against me. Winnie definitely knew what she was doing. I wanted to ask her (in between spasms of sheer ecstasy) where she learned to do what she was doing to me, but even I knew it was the wrong time for a question like that. Or any question, for that matter. So I just relaxed and let her go at it.

Winnie sucked my cock like a champ, making occasional moaning noises as she went down on me, and in an embarrassingly short time I was right on the verge of orgasm. I thought about saying something to her, warning her so she could pull away before the critical moment, but I stayed selfishly silent, and when I finally did go off my come squirted right into her talented mouth. Winnie didn't even seem surprised; she just took it all in, patiently holding the end of my cock in her mouth until I was done. Then she pulled away, swallowed, and laid her head on my chest as she tucked my cock back into my pants. I put my hand on top of her head, caressed her glossy black hair, and wondered if I should ask her now or just keep my big mouth shut.

No, I couldn't keep my mouth shut. This was too big, too important. This was something I should have already known about her.

"Winnie..." I said.

"You got any gum?" Winnie asked.

"Uh...yeah, I think so."

I found a few sticks in my jacket pocket and handed her one. She unwrapped the gum nonchalantly, stuck it in her mouth, and started chewing.

"Um, Winnie?" I said.

"Hmm?" Winnie replied, her jaw working rhythmically.

"Well, I kinda want to ask you something. But I'm not, like, criticizing or anything. I just want to know. You know?" Winnie just stared at me, so I pressed on. "Well, I, um, I guess I'm just sort of wondering...where did you learn to do that?"

Winnie looked away, then down at her lap. She was silent for several long moments and I was afraid I'd overstepped my bounds, even though I knew I hadn't. Not really. Finally, she looked out the window and said, "I guess I should have told you this a long time ago, Kevin. But I could never figure out how to say it. I didn't want you to be hurt or jealous." She paused so long I wondered if she was actually going to continue or not. "Kevin...Brian taught me."

Brian who?

"Brian who?" I said. And then it hit me. "You mean your brother Brian?" Winnie didn't answer, which was pretty much all the answer I needed. "But Winnie, Brian died four years ago. You were only twelve then."

"Yeah..." Winnie said.

"You mean he taught you how to...do that...when you were only twelve?"

"Actually, I was ten when it started." Winnie looked at me with hurt in her eyes. "I don't really want to talk about it right now, Kevin. I can't. Okay? I'm sorry."

And there it was. That old familiar pain of hers: her brother. It was the central reason for all of Winnie's sadnesses, everything that never worked out in her life, everything that had ever gone wrong. The justification for every mistake or willfully bad thing she'd ever done. I had come to think of it as a tired excuse, but it was still a good one, still a problem I couldn't fight, a wound that I could never help her heal from.

It didn't feel fair to me, but what could I do about it?

"Winnie-"

Winnie suddenly threw her arms around me and kissed me deeply, and as she kissed me I felt her grab my wrist and guide my hand down between her legs. And not just between her legs; right up her dress and to her pussy. She even made me start rubbing her through her panties. She moaned into my mouth and breathed excitedly through her nose, acting almost like she was out of control, and even though I knew part of what she was doing was just a way to distract me, I decided we could talk about...whatever it was we were talking about...some other time.

I wormed my fingers under her panties and found her pussy. It was warm and wet, more so than I'd ever noticed before, and as I began to slowly move my fingers through her pubic hair, touching and caressing her tender lips, Winnie gasped into my mouth and opened her legs a little wider. She had been pushing her tongue in and out of my mouth (her gum was mysteriously gone), but now she took my tongue into her mouth and started sucking it as skillfully as she'd sucked my cock.

Speaking of which: it was standing at attention again, hard as a rock. As if she could sense my newly returned desire, Winnie let one of her hands move back down to my crotch and she started stroking me through my jeans. Really squeezing and pulling on it. She was more passionate than I'd ever seen her before.

As was our habit, I guided Winnie down onto her back. laying sort of next to her and on her at the same time. Winnie pulled her dress up to her waist, then worked a little clumsily to get her underwear off. Then she spread her legs and we went back to kissing while I rubbed her pussy with my fingertips, bringing her to two shuddering orgasms.

Afterward, Winnie, breathing hard and sounding like she was about to cry, said, "Oh God, Kevin, that was beautiful."

You bet your bippy it was. But it wasn't over. Not by a longshot. I pressed my mouth down onto Winnie's lips and pushed my tongue into her mouth, and as I kissed her I rolled on top of her. I moved so fast that she didn't get the chance to close her legs, so now my crotch was square with hers, my aching hardon pressing down onto her still fluttering pussy.

Winnie pulled her mouth away from mine and said, "Kevin," that note of warning in her voice.

But I wasn't listening to it this time. I pressed my mouth back down onto hers and reached for my fly. I got my pants undone and took out my cock and, with Winnie struggling minutely under me, I guided it up to her pussy. Winnie gasped when she felt the head pressing against her, and even moaned a little when I started to push it inside of her, but I couldn't tell if it was a good moan or a bad moan. To be honest, it didn't make much of a difference to me.

I did notice, though, that the more of my cock I got into her, the less Winnie resisted. She was surrendering to me, though how reluctantly, I couldn't tell. I got the end of my cock into her, then a little more, and a little more. I slid into her inexorably, amazed and delighted by the moist warmth suddenly surrounding me, by the sensation of Winnie's slowly yielding pussy. Winnie was now returning my kisses, and by the time I got it all the way into her she had her arms around my neck and she was sucking on my tongue again.

Of course, I noticed that Winnie wasn't a virgin, but I was too preoccupied at the moment to give that fact much consideration. Instead, I just started fucking her, pushing my cock into Winnie's delicious body over and over again, and in my mind I kept thinking, I'm fucking Winnie Cooper, I'm fucking Winnie Cooper. It was the ultimate dream of my entire life coming true.

Winnie responded passionately to this new development in our relationship, moving and writhing under me, pushing her pussy back against my cock, letting me drive deeper and deeper into her. She sighed and moaned, murmured, "Yes, yes, yes," in time with my thrusts, dug her fingernails into my back and wrapped her slim legs around my waist. She held on with suddenly powerful arms as I repeatedly shoved my cock into her, and I could tell that she came at least once while I was fucking her.

I wished I could just keep fucking her forever. That I would never have to come, never have to stop, never have to go on with my dreary life. Eternity between the legs of my best girl seemed like Heaven to me. But, of course, all impossibly good things have to end sooner or later. Even sex with Winnie Cooper.

I could feel it building inside of me and thought about pulling out, so that at least we wouldn't have to worry about pregnancy, but at the last possible moment I went the other way, pushing as deep as I could into Winnie's pussy. My balls slammed against her butt and my cock began to throb as my come poured into her. Wave after wave after wave of it. It was the most exquisite orgasm I'd ever had, would probably ever have for the rest of my life.

When it was over Winnie and I both collapsed, exhausted and sweaty and breathing like we'd just run a mile. The smell of sex was strong in the air, and though I couldn't see them, I was sure our windows were fogged up like crazy.

I don't know how long we lay there, only that it was some time later that Winnie kissed me, hugged me, and told me that she loved me. I told her I loved her too, we kissed a little bit more, then we got ourselves straightened out and ready to go back home. And on the drive back to Winnie's house neither one of us said a word.

*****

At least until I parked at the curb and turned off the engine. I turned to Winnie and said, "I know you probably don't want to talk about it, but I have to ask, Winnie. That wasn't your first time, was it?"

"No," Winnie said, putting on that mask of sadness again. "I'm sorry, Kevin. I know I should have told you."

"So, who was it? Who was your first guy?"

"It was Brian again."

Winnie's answer was so unexpected and incredible that I almost asked Brian who again.

"Your own brother?" I said. "How could he do something like that, Winnie? How could he hurt you that way? I'm sorry, I know you worship the ground he walked on, but this goes way beyond anything that somebody could....could..." What? Comprehend? Forgive?

"He didn't hurt me, Kevin," Winnie said. "But I can't say anything more. I just can't. Please try to understand..."

"I'm sorry, Winnie, but I don't understand. At least, not entirely." I was suddenly thinking of my own sexual feelings for Karen. "I mean, if you were my sister, I would probably want you too, but...I don't know if I could...you know..."

"Please let's not talk about it anymore," Winnie said. She wiped a tear from her eye. "I think I'll go in now."

"Winnie, we need to talk about this."

"No, we don't. Good night, Kevin."

And with that, Winnie got out of the car, slammed the door, and ran up to her house. I watched her go with a sinking feeling inside of me. Our relationship had just gone beyond any summit we had ever reached before, took on a new definition and meaning, went careening through new territories; it should have been a new and brilliant beginning for us. Instead, it had all come crashing down again, crushed by the weight of Winnie's secrets. Her lies. It wasn't my fault this time, or at least I didn't think it was, but as I drove home in the night, feelings swirling within me as I stared out at the road, that knowledge didn't make things any better.

Sometimes, with some people, things never really are as right as they should be. And as much as I wished for it and dreamed about it, I knew now that things never would be as right as they could be between me and Winnie. It was too bad, because she really was my best girl.

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